3,5-dibromo-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamide → 3,5-dibromo-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methylbenzamide

HRID 749462Notes

Reaction equation

HRID 749462 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Br:24])[CH:23]=1)[C:5]([N:7]([CH2:9][C@H:10]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH2:11][CH:12]=C)[CH3:8])=[O:6].FC1C=CC([C@H](CC=C)CN(C)C(=[O:50])C2C=C(C(F)(F)F)C=C(C(F)(F)F)C=2)=CC=1>>[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Br:24])[CH:23]=1)[C:5]([N:7]([CH2:9][C@H:10]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH2:11][CH:12]=[O:50])[CH3:8])=[O:6]

Participants

3

Reactant 2

HCID 689767873,5-dibromo-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamideHCID 86606886N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide

Product 1

HCID 586835303,5-dibromo-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methylbenzamide

Procedure

The compound was synthesized in an analogous way to that of Method 20b but using 3,5-dibromo-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamide rather than N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (yield, 96%). 1H NMR (400 MHz, CDCl3): 2.6-3.9 (cm, 8H), 6.8-8.2 (cm, 7H), 9.8 (s, 1H).

Workup

  1. customThe compound was synthesized in an analogous way to that of Method 20b

Sources & evidence

ORD record
ord-5d88cff8c309411e9acb19d58c929e0f
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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