4-(Bromomethyl)-3-fluorobenzonitrile → HCID 66653037, compound

HRID 572566Notes

Reaction equation

HRID 572566 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[C:5]([F:11])[CH:4]=1)#[N:2].[NH2:12][CH:13]([CH2:21][CH3:22])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:12][CH:13]([CH2:21][CH3:22])[C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])=[C:5]([F:11])[CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 27831494-(Bromomethyl)-3-fluorobenzonitrileHCID 13283519tert-Butyl 2-aminobutanoate

Product 1

HCID 66653037HCID 66653037, compound

Procedure

The title compound was prepared following the general procedure 10 starting from 4-cyano-2-fluoro-benzylbromide (Fluorochem, 8.2 g, 38 mmol) and tert-butyl 2-aminobutanoate (6.2 g, 38 mmol), obtained in step 1. It was isolated as a colorless liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.79-7.76 (d, J=10.2 Hz, 1H), 7.68-7.67 (t, J=2.1 Hz, 2H), 3.84-3.79 (m, 1H) 3.71-3.66 (m, 1H), 2.95-2.91 (m, 1H), 2.52-2.48 (m, 1H), 1.58-1.53 (m, 2H), 1.49 (s, 9H), 0.87-0.83 (m, 3H).

Workup

  1. customobtained in step 1
  2. customIt was isolated as a colorless liquid

Sources & evidence

ORD record
ord-cc720b4a76964e059f10b935eb6b069e
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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