3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester → {(S)-6-[(R)-7-fluoro-4-(3,6-dihydropyran-4-yl-pyridin-3-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 237625Notes

Reaction equation

HRID 237625 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([C:25]5[C:26](Br)=[N:27][CH:28]=[CH:29][CH:30]=5)[CH:20]=[CH:21][C:22]=4[F:24])[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.CC1(C)C(C)(C)OB([C:41]2[CH2:42][CH2:43][O:44][CH2:45][CH:46]=2)O1>>[CH3:1][O:2][C:3](=[O:32])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([C:25]5[C:26]([C:41]6[CH2:46][CH2:45][O:44][CH2:43][CH:42]=6)=[N:27][CH:28]=[CH:29][CH:30]=5)[CH:20]=[CH:21][C:22]=4[F:24])[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.[F:24][C:22]1[CH:21]=[CH:20][C:19]([C:25]2[C:26]([C:41]3[CH2:42][CH2:43][O:44][CH2:45][CH:46]=3)=[N:27][CH:28]=[CH:29][CH:30]=2)=[C:18]2[C:23]=1[C@H:15]([O:14][C:12]1[CH:11]=[CH:10][C:9]3[C@H:5]([CH2:4][C:3]([OH:32])=[O:2])[CH2:6][O:7][C:8]=3[CH:13]=1)[CH2:16][CH2:17]2

Participants

4

Reactant 2

HCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 86697291{(S)-6-[(R)-4-(2-Bromo-pyridin-3-yl)-7-fluoro-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Product 2

HCID 86697297{(S)-6-[(R)-7-fluoro-4-(3,6-dihydropyran-4-yl-pyridin-3-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl esterHCID 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

Procedure

The methyl ester of the title compound is prepared from {(S)-6-[(R)-4-(2-bromo-pyridin-3-yl)-7-fluoro-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydropyran following a procedure analogous to that described in Step 1 of Intermediate 56. Saponification of the methyl ester, {(S)-6-[(R)-7-fluoro-4-(3,6-dihydropyran-4-yl-pyridin-3-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester, gives the title compound following a procedure analogous to that described for Example 4. LC (method 9): tR=0.93 min; Mass spectrum (ESI+): m/z=488 [M+H]+.

Sources & evidence

ORD record
ord-8d4071752fe2427e9a8080cc380aef3f
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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