N-bromobutanimide → (S)-1-(1-{[4-(bromoacetyl)-2-cyanoquinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

HRID 2422540Notes

Reaction equation

HRID 2422540 reaction equation
[N+:1]([C:4]1[CH:42]=[CH:41][C:7]([C:8]([O:10][C@@:11]([C:18]2[N:19]=[N:20][N:21]([CH2:23][C:24]3[CH:33]=[C:32]4[C:27]([C:28]([C:36]([O:38]CC)=[CH2:37])=[CH:29][C:30]([C:34]#[N:35])=[N:31]4)=[CH:26][CH:25]=3)[CH:22]=2)([C:14]([F:17])([F:16])[F:15])[CH2:12][CH3:13])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1C(=O)N([Br:50])C(=O)C1>C1COCC1.O>[N+:1]([C:4]1[CH:42]=[CH:41][C:7]([C:8]([O:10][C@@:11]([C:18]2[N:19]=[N:20][N:21]([CH2:23][C:24]3[CH:33]=[C:32]4[C:27]([C:28]([C:36](=[O:37])[CH2:38][Br:50])=[CH:29][C:30]([C:34]#[N:35])=[N:31]4)=[CH:26][CH:25]=3)[CH:22]=2)([C:14]([F:17])([F:16])[F:15])[CH2:12][CH3:13])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 66791347(S)-1-(1-{[2-cyano-4-(1-ethoxyvinyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

Product 1

HCID 86621977(S)-1-(1-{[4-(bromoacetyl)-2-cyanoquinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-1-(1-{[2-cyano-4-(1-ethoxyvinyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate (593 mg, 1.05 mmol) in THF (4 ml) and water (0.25 ml) was added NBS (205 mg, 1.16 mmol). The mixture was stirred at room temperature for 30 min. The solution was then evaporated to dryness and purified by flash chromatography (eluting solvent: 3% acetone in dichloromethane) to afford the title compound. 1H NMR (400 MHz, acetone-d6): δ 8.55 (s, 1H), 8.50 (s, 1H), 8.40 (d, 2H), 8.37 (d, 1H), 8.30 (d, 2H), 8.07 (s, 1H), 7.85 (d, 1H), 6.05 (s, 2H), 5.05 (s, 2H), 3.05 (m, 1H), 2.85 (m, 1H), 1.15 (t, 3H).

Workup

  1. customThe solution was then evaporated to dryness
  2. custompurified by flash chromatography (eluting solvent: 3% acetone in dichloromethane)

Sources & evidence

ORD record
ord-f324046ce9d94a8db06662d8c8abed63
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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