1-(Bromomethyl)-3-(trifluoromethyl)benzene → 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{4-[3-(trifluoromethyl)benzyl]benzyl}benzamide

HRID 2090091Notes

Reaction equation

HRID 2090091 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:37]([CH3:39])[CH3:38])[C:6]2[O:10][C:9]([C:11]3[CH:35]=[CH:34][C:14]([C:15]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22](B5OC(C)(C)C(C)(C)O5)=[CH:21][CH:20]=4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:36]=1)#[N:2].Br[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([C:48]([F:51])([F:50])[F:49])[CH:43]=1.C(B(O)O)(C)=C>>[C:1]([C:3]1[CH:4]=[C:5]([CH:37]([CH3:39])[CH3:38])[C:6]2[O:10][C:9]([C:11]3[CH:35]=[CH:34][C:14]([C:15]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([CH2:41][C:42]5[CH:47]=[CH:46][CH:45]=[C:44]([C:48]([F:49])([F:50])[F:51])[CH:43]=5)=[CH:21][CH:20]=4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:36]=1)#[N:2]

Participants

4

Reactant 3

HCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 10855372(Prop-1-en-2-yl)boronic acidHCID 251536354-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]benzamide

Product 1

HCID 251525824-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{4-[3-(trifluoromethyl)benzyl]benzyl}benzamide

Procedure

The title compound was prepared from 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]benzamide (26 mg, EXAMPLE 8) and 1-(bromomethyl)-3-(trifluoromethyl)benzene (24 mg) following the procedure described in EXAMPLE 3 (26 mg, 93%) Mass spectrum (ESI) 554.2 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.33 (d, J=8.2 Hz, 2H), 7.97 (d, J=8.3 Hz, 2H), 7.94 (s, 1H), 7.51 (s, 1H), 7.41 (m, 4H), 7.33 (d, J=8.0 Hz, 2H), 7.20 (d, J=7.8 Hz, 2H), 6.42 (bs, 1H), 4.67 (d, J=5.5 Hz, 2H), 4.04 (s, 2H), 3.38 (sept, J=6.9 Hz, 1H), 1.46 (d, J=6.8, 6H).

Sources & evidence

ORD record
ord-aaca2ad26c8841d8bb94d443c80b675d
Source dataset
uspto-grants-2013_05
Patent number
US08436028B2

Reaction notes

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