{(S)-6-[(R)-7-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester → Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(tetrahydro-2H-pyran-4-yloxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 237452Notes

Reaction equation

HRID 237452 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5](B2OC(C)(C)C(C)(C)O2)=[C:6]2[C:10]=1[C@H:9]([O:11][C:12]1[CH:25]=[CH:24][C:15]3[C@H:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:17][O:18][C:14]=3[CH:13]=1)[CH2:8][CH2:7]2.Br[C:36]1[C:48]([CH3:49])=[CH:47][C:39]([O:40][CH:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)=[CH:38][C:37]=1[CH3:50]>>[CH3:50][C:37]1[CH:38]=[C:39]([O:40][CH:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[CH:47]=[C:48]([CH3:49])[C:36]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[C:10]2[C:6]=1[CH2:7][CH2:8][C@H:9]2[O:11][C:12]1[CH:25]=[CH:24][C:15]2[C@H:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:17][O:18][C:14]=2[CH:13]=1

Participants

3

Reactant 2

HCID 86697106{(S)-6-[(R)-7-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl esterHCID 866971154-(4-Bromo-3,5-dimethylphenoxy)tetrahydro-2H-pyran

Product 1

HCID 86697116Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(tetrahydro-2H-pyran-4-yloxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Procedure

The title compound is prepared from methyl 2-((S)-6-((R)-7-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate and 4-(4-bromo-3,5-dimethylphenoxy)tetrahydro-2H-pyran following a procedure analogous to that described in Step 5 of Intermediate 1. LC (method 4): tR=1.92 min; Mass spectrum (ESI+): m/z=569 [M+Na]+.

Sources & evidence

ORD record
ord-82b933069f4f44e4a4e3a0e79f3961c1
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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