(3-Bromopropoxy)(tert-butyl)dimethylsilane → 4-[(2,2-Dimethylpropyl)(3-hydroxypropyl)amino]-2-(trifluoromethyl)benzonitrile

HRID 1173454Notes

Reaction equation

HRID 1173454 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][NH:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1.Br[CH2:20][CH2:21][CH2:22][O:23][Si](C(C)(C)C)(C)C>>[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][N:4]([CH2:20][CH2:21][CH2:22][OH:23])[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:14])([F:15])[F:16])[CH:6]=1

Participants

3

Reactant 2

HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 112075814-[(2,2-Dimethylpropyl)amino]-2-(trifluoromethyl)benzonitrile

Product 1

HCID 113475544-[(2,2-Dimethylpropyl)(3-hydroxypropyl)amino]-2-(trifluoromethyl)benzonitrile

Procedure

Synthesized as described in Example 1B from 4-[(2,2-dimethylpropyl)amino]-2-(trifluoromethyl)benzonitrile and [(3-bromopropyl)oxy](1,1-dimethylethyl)dimethylsilane: 1H NMR (300 MHz, CDCl3) δ 7.53 (d, J=8.9 Hz, 1H), 7.05 (d, J=2.5 Hz, 1H), 6.87 (dd, J=8.9, 2.5 Hz, 1H), 3.70 (app. bq, J=4.7 Hz, 2H), 3.62 (app. t, J=7.3 Hz, 2H), 3.27 (s, 2H), 1.87-1.75 (m, 2H), 1.47 (bt, J=4.2 Hz, 1H), 0.99 (s, 9H).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-750f451932c64721b148b18d19b17765
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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