{(S)-6-[(R)-4-bromo-7-fluoro-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester → Methyl 2-((S)-6-((R)-4-(4-(2,5-dihydrofuran-3-yl)-2,6-dimethylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 237583Notes

Reaction equation

HRID 237583 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:41]([CH3:42])=[CH:40][C:39]([C:43]2[CH2:44][O:45][CH2:46][CH:47]=2)=[CH:38][C:37]=1[CH3:48].BrC1C=CC(F)=C2C=1CC[C@H]2OC1C=CC2[C@H](CC(OC)=O)COC=2C=1>>[O:45]1[CH2:46][CH:47]=[C:43]([C:39]2[CH:38]=[C:37]([CH3:48])[C:36]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[C:10]4[C:6]=3[CH2:7][CH2:8][C@H:9]4[O:11][C:12]3[CH:25]=[CH:24][C:15]4[C@H:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:17][O:18][C:14]=4[CH:13]=3)=[C:41]([CH3:42])[CH:40]=2)[CH2:44]1

Participants

4

Reactant 3

HCID 86697103{(S)-6-[(R)-4-bromo-7-fluoro-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl esterHCID 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 866972463-(4-Bromo-3,5-dimethylphenyl)-2,5-dihydrofuran

Product 1

HCID 86697247Methyl 2-((S)-6-((R)-4-(4-(2,5-dihydrofuran-3-yl)-2,6-dimethylphenyl)-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-dihydro-benzofuran-3-yl)acetate and 3-(4-bromo-3,5-dimethylphenyl)-2,5-dihydrofuran following a procedure analogous to that described in Step 5 of Intermediate 1. LC (method 9): tR=1.26 min; Mass spectrum (ESI+): m/z=515 [M+H]+.

Sources & evidence

ORD record
ord-ac47e98b30cc4220b2f0099bb10fb3fa
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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