2-Bromobenzyl bromide → HCID 68972496, compound

HRID 1726245Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:25]#[N:26])[C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].CC([N-]C(C)C)C.[Br:35][C:36]1[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=1[CH2:38]Br>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]([C:25]#[N:26])([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:17][CH:16]=2)[CH2:38][C:37]2[CH:40]=[CH:41][CH:42]=[CH:43][C:36]=2[Br:35])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of the above nitrile (280 mg, 0.76 mmol) in THF at −78° C. was added freshly prepared LDA (0.32M, 2.6 mL, 0.83 mmol). The resulting mixture was stirred for 30 min. at −78° C. and 2-bromobenzyl bromide (570 mg, 2.28 mmol) in THF (1 mL) was added. The reaction was stirred for 3 hours at 0° C. and quenched with saturated aqueous NH4Cl (20 mL) to give 4-[2-(2-bromo-phenyl)-1-cyano-1-(4-trifluoromethyl-phenyl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester (264 mg, 65%) as a white foam after work-up and purification.

Workup

stirringThe reaction was stirred for 3 hours at 0° C.
customquenched with saturated aqueous NH4Cl (20 mL)

Sources & evidence

ORD record: ord-431b2c9f5f0d4953a67195995e3426dd
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

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