4-(Bromomethyl)benzonitrile → HCID 66678260, compound
Reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1)#[N:2].[CH3:11][NH:12][CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:12]([CH3:11])[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])=[CH:5][CH:4]=1)#[N:2]Participants
3
Procedure
The title compound was prepared following the general procedure 10, starting from 4-cyanobenzyl bromide (1.5 g, 7.7 mmol) and tert-butyl N-methyl-beta-alaninate (1.5 g, 9.2 mmol, prepared as described in Biorg. Med. Chem. (11) 2003, 3083-3099). It was isolated as a yellow oil (1.9 g, 89%). 1H NMR (DMSO-d6, 300 MHz) δ 7.78 (d, J=8.3 Hz, 2H), 7.49 (d, J=8.3 Hz, 2H), 3.55 (s, 2H), 2.60 (t, J=6.9 Hz, 2H), 2.38 (t, J=6.9 Hz, 2H), 2.11 (s, 3H), 1.39 (s, 9H). LC/MS (Method B): 275.0 (M+H)+. HPLC (Method A) Rt 2.40 min (Purity: 82.5%).
Sources & evidence
- ORD record
- ord-3b65baa7885e41978ebbc178d1b0a9f0
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802704B2
Reaction notes
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