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

HRID 1173391Notes

Reaction equation

HRID 1173391 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:7]=2)[CH2:3][CH2:2]1.Br[CH2:19][CH2:20][CH2:21][O:22][Si](C(C)(C)C)(C)C>>[CH:1]1([CH2:4][N:5]([CH2:19][CH2:20][CH2:21][OH:22])[C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([C:14]([F:15])([F:16])[F:17])[CH:7]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 114818514-[(Cyclopropylmethyl) amino]-2-(trifluoromethyl)benzonitrile

Product 1

HCID 114607194-[(Cyclopropylmethyl)(3-hydroxypropyl)amino]-2-(trifluoromethyl)benzonitrile

Procedure

Synthesized as described in Example 1B from 4-[(cyclopropylmethyl) amino]-2-(trifluoromethyl)benzonitrile and [(3-bromopropyl)oxy](1,1-dimethylethyl)dimethylsilane: 1H NMR (300 MHz, CD3OD) δ 7.63 (d, J=8.7 Hz, 1H), 7.11 (d, J=2.6 Hz, 1H), 7.02 (dd, J=9.0, 2.7 Hz, 1H), 3.66-3.56 (m, 4H), 3.37 (d, J=6.4 Hz, 2H), 1.83 (tt, J=7.2, 6.2 Hz, 2H), 1.13-0.98 (m, 1H), 0.64-0.53 (m, 2H), 0.37-0.28 (m, 2H); MS (APCI) m/z 299 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-debb7e78a4784074bb372041f542e2a7
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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