2-bromo-N,N-dimethylbenzamide → HCID 86697287, compound

HRID 237615Notes

Reaction equation

HRID 237615 reaction equation
Br[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].[F:13][C:14]1[CH:15]=[CH:16][C:17](B2OC(C)(C)C(C)(C)O2)=[C:18]2[C:22]=1[C@H:21]([O:23][C:24]1[CH:37]=[CH:36][C:27]3[C@H:28]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:29][O:30][C:26]=3[CH:25]=1)[CH2:20][CH2:19]2.BrC1C=CC(F)=C2C=1CC[C@H]2OC1C=CC2[C@H](CC(OC)=O)COC=2C=1>>[CH3:7][N:6]([CH3:8])[C:4]([C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[C:17]1[CH:16]=[CH:15][C:14]([F:13])=[C:22]2[C:18]=1[CH2:19][CH2:20][C@H:21]2[O:23][C:24]1[CH:37]=[CH:36][C:27]2[C@H:28]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:29][O:30][C:26]=2[CH:25]=1)=[O:5]

Participants

4

Reactant 3

HCID 32643422-bromo-N,N-dimethylbenzamideHCID 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 ester

Product 1

HCID 86697287HCID 86697287, compound

Procedure

The title compound is prepared from 2-bromo-N,N-dimethylbenzamide and 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 following a procedure analogous to that described in Step 5 of Intermediate 1. LC (method 9): tR=1.14 min; Mass spectrum (ESI+): m/z=490 [M+H]+.

Sources & evidence

ORD record
ord-4c42763888ba4b469eb74ee3326dcbc3
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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