{(S)-6-[(R)-7-Fluoro-4-(2-(3,6-dihydropyran-4-yl)-pyridin-3-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid → {(S)-6-[(R)-7-Fluoro-4-(2-tetrahydropyran-4-yl-pyridin-3-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid

HRID 237725Notes

Reaction equation

HRID 237725 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]2[C:26]([C:31]3[CH2:32][CH2:33][O:34][CH2:35][CH:36]=3)=[N:27][CH:28]=[CH:29][CH:30]=2)=[C:6]2[C:10]=1[C@H:9]([O:11][C:12]1[CH:24]=[CH:23][C:15]3[C@H:16]([CH2:19][C:20]([OH:22])=[O:21])[CH2:17][O:18][C:14]=3[CH:13]=1)[CH2:8][CH2:7]2>[Pd].CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]2[C:26]([CH:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[N:27][CH:28]=[CH:29][CH:30]=2)=[C:6]2[C:10]=1[C@H:9]([O:11][C:12]1[CH:24]=[CH:23][C:15]3[C@H:16]([CH2:19][C:20]([OH:22])=[O:21])[CH2:17][O:18][C:14]=3[CH:13]=1)[CH2:8][CH2:7]2

Participants

4

Reactant 1

HCID 86697298{(S)-6-[(R)-7-Fluoro-4-(2-(3,6-dihydropyran-4-yl)-pyridin-3-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid

Product 1

HCID 86697395{(S)-6-[(R)-7-Fluoro-4-(2-tetrahydropyran-4-yl-pyridin-3-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of {(S)-6-[(R)-7-fluoro-4-(2-(3,6-dihydro-pyran-4-yl)-pyridin-3-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid (30 mg), 10% palladium on carbon (10 mg) and methanol (3 mL) is shaken under hydrogen atmosphere (3 bar) at room temperature for 12 h. The mixture is filtered over Celite and the filtrate is concentrated to give the title compound. LC (method 9): tR=0.96 min; Mass spectrum (ESI+): m/z=490 [M+H]+.

Workup

  1. filtrationThe mixture is filtered over Celite
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-c8ce9e7571ab436686f1b7c9467d3951
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

Loading…