Method of making tetrahydronaphthyridinyl nonanoic acid compounds

A method of making a compound of formula I:

• or a pharmaceutically acceptable salt or solvate thereof, comprising:
• Step 1:
• reacting Compound A:
• wherein “Ac” refers to an acetyl group and is a sub stituent on W, with Compound B:
• wherein X1 is halogen, and R21, R22, R23, and R31 are each independently selected from the group consisting of optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, and optionally substituted aryl, to form Compound 1:
• and
• Step 2:
• reducing Compound 1:
• optionally in the presence of a catalyst, to form the compound of formula I:
• wherein:
• Q is
• X is CR4 or N;
• Y is CR4 or N;
• R1 is H, F, Cl, C1-C4 alkyl substituted with 1, 2, 3, 4, 5, 6, 7, 8, or 9 fluorine atoms, or C1-C4 alkoxy substituted with 0, 1, 2, 3, 4, 5, 6, or 7 fluorine atoms;
• R2 and R3 are each independently H, F, CH2F, CHF2, or CF3, provided that one of R2 and R3 is not H;
• each R4 is independently H, CH2F, CHF2, or CF3;
• and
• R51 and R52 are each independently H, F, or Cl;
• W is fused to the pyridyl moiety at positions 1 and 2, and W is a 5- to 7-membered ring optionally comprising 1-4 heteroatoms selected from the group consisting of N, O, and S;
• n is 1 or 2;
• and
• R and R′ are each independently H or F, or R and R′, together with the carbon atom to which they are attached, form a 3- or 4-membered carbocyclic or heterocyclic ring.