3,5-Dichloro-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamide → 6-Cyano-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methylindane-4-carboxamide

HRID 749479Notes

Reaction equation

HRID 749479 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:12]([N:14]([CH2:16][C@H:17]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:18][CH:19]=C)[CH3:15])=[O:13])[C:6]2[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1)#[N:2].ClC1C=C(C=C(Cl)C=1)C(N(C[C@H](C1C=CC(F)=CC=1)CC=C)C)=[O:33]>>[C:1]([C:3]1[CH:4]=[C:5]([C:12]([N:14]([CH2:16][C@H:17]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:18][CH:19]=[O:33])[CH3:15])=[O:13])[C:6]2[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1)#[N:2]

Participants

3

Reactant 2

HCID 689786383,5-Dichloro-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamideHCID 689790206-cyano-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylindane-4-carboxamide

Product 1

HCID 112222716-Cyano-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methylindane-4-carboxamide

Procedure

The compound was synthesized in an analogous way to that of Method 21b but using 6-cyano-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylindane-4-carboxamide rather than 3,5-dichloro-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamide (yield, 89%). 1H NMR (300 MHz, CDCl3): 0.9-4.2 (cm, 14H), 5.9 (s, <1H), 6.6-8.2 (cm, 6H), 8.0 (s, <1H), 9.8 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-e9016bc704ad4e52b031bf2fa137d724
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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