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

HRID 749463Notes

Reaction equation

HRID 749463 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([I: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].ClC1C=C(C=C(Cl)C=1)C(N(C[C@H](C1C=CC(F)=CC=1)CC=C)C)=[O:30]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([I: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:30])[CH3:8])=[O:6]

Participants

3

Reactant 2

HCID 689770113-bromo-N-[(2S)-2-(4-fluorophenyl)pent-4en-1-yl]-5-iodo-N-methylbenzamideHCID 689786383,5-Dichloro-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamide

Product 1

HCID 586835213-bromo-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-5-iodo-N-methylbenzamide

Procedure

The compound was synthesized in an analogous way to that of Method 21b but using 3-bromo-N-[(2S)-2-(4-fluorophenyl)pent-4en-1-yl]-5-iodo-N-methylbenzamide rather than 3,5-dichloro-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamide (yield, 100%). 1H NMR (500 MHz, CDCl3): 2.6-3.2 (cm, 4H), 3.4-3.9 (cm, 2H), 4.0-4.2, (cm, 2H), 6.8-8.2 (cm, 7H), 9.8 (s, 1H).

Workup

  1. customThe compound was synthesized in an analogous way to that of Method 21b

Sources & evidence

ORD record
ord-858dc88cdb664b3fbb8d9b27fafc17e4
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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