4-(Bromoacetyl)benzonitrile → HCID 18707469, compound

HRID 1421909Notes

Reaction equation

HRID 1421909 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][C:8]2([CH2:26][C:27]3[N:28]([CH3:32])[CH:29]=[N:30][CH:31]=3)[NH:12][C:11](=[S:13])[N:10]([CH2:14][CH:15]3[CH2:20][CH:19]4[CH2:21][CH:17]([C:18]4([CH3:23])[CH3:22])[CH:16]3[CH3:24])[C:9]2=[O:25])=[CH:5][N:4]=[CH:3]1.[C:33]([C:35]1[CH:44]=[CH:43][C:38]([C:39](=[O:42])[CH2:40]Br)=[CH:37][CH:36]=1)#[N:34].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>>[CH3:32][N:28]1[C:27]([CH2:26][C:8]2([CH2:7][C:6]3[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=3)[C:9](=[O:25])[N:10]([CH2:14][CH:15]3[CH2:20][CH:19]4[CH2:21][CH:17]([C:18]4([CH3:22])[CH3:23])[CH:16]3[CH3:24])[C:11]([S:13][CH2:40][C:39]([C:38]3[CH:43]=[CH:44][C:35]([C:33]#[N:34])=[CH:36][CH:37]=3)=[O:42])=[N:12]2)=[CH:31][N:30]=[CH:29]1

Participants

4

Reactant 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 3251421Potassium bis(trimethylsilyl)amideHCID 21266562HCID 21266562, compound

Product 1

HCID 18707469HCID 18707469, compound

Procedure

Using the same procedure as described in example 1D, the title compound of 3C (0.355 g, 0.78 mmol) and 4-cyanophenacyl bromide (193 mg, 0.86 mmol) in the presence of potassium bis(trimethylsilyl)-amide (193 mg, 0.86 mmol) reacted to yield 0.232 g (0.39 mmol, 50% yield) of the title compound of example 3D after chromatographic purification. Cl-Ms: m/z 598.3 [M+1].

Sources & evidence

ORD record
ord-59613e4147f544129ce8ed89c9bf04e4
Source dataset
uspto-grants-2000_06
Patent number
US06080769

Reaction notes

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