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US 10,093,806 B2Granted
Methods for synthesizing rhodamine dyes
AssigneePromega Corporation
InventorsStephen J. Dwight, Sergiy Levin
Life of this patent
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Abstract
Described herein are methods for the regioselective synthesis of substituted rhodamine dyes.
Claims20
A method of synthesizing a rhodamine dye, the method comprising:
- reacting a compound of formula (I):
- wherein
- R1 and R2 are each independently hydrogen, alkyl, or R1a—CO—, wherein R1a is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxy;
- or R1 and R2, together with the atoms to which they are attached, form a 3-8 membered ring;
- Rc is selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl and halogen;
- and
- Ra and Rb are each independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl and halogen;
- or
- R1 and Ra, together with the atoms to which they are attached, form a 5-8 membered ring, and
- R2 and Rb, together with the atoms to which they are attached, form a 5-8 membered ring;
- with a compound of formula (II),
- wherein
- R is selected from the group consisting of halogen, alkyl, haloalkyl, cyano, carboxy, alkoxy, haloalkoxy, alkoxycarbonyl, (carboxyl)heteroalkyl, alkylcarbonyl, alkoxyalkyl, cycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, sulfonate, sulfonamide and amide;
- n is 0, 1, 2, 3 or 4;
- X is halogen or OR3;
- and R3 is selected from the group consisting of hydrogen, alkyl, aryl, alkylcarbonyl, alkoxycarbonyl, haloalkyl, haloalkylcarbonyl, haloalkoxycarbonyl, alkylsulfonyl, arylsulfonyl and haloalkylsulfonyl;
- to form the rhodamine dye.
14 more elements
Dependencies are inferred from the claim text.