3-(Bromomethyl)thiophene → 4-[(4-Cyano-phenyl)-thiophen-3-ylmethyl-amino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1726289Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br[CH2:34][C:35]1[CH:39]=[CH:38][S:37][CH:36]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH2:34][C:35]2[CH:39]=[CH:38][S:37][CH:36]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 4-(4-cyano-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (see EXAMPLE 106) (1.17 g, 3.89 mmol) in THF (20 mL) cooled to −78° C. was added KHMDS (0.5M, 12.0 mL, 6.0 mmol) and the mixture was stirred at −78° C. for 20 minutes. The reaction was quenched with 3-(bromomethyl)thiophene (1.06 g, 5.99 mmol) and warmed to room temperature to afford 4-[(4-cyano-phenyl)-thiophen-3-ylmethyl-amino]-piperidine-1-carboxylic acid tert-butyl ester (941 mg, 61%) following work-up and purification.

Workup

temperaturewarmed to room temperature

Sources & evidence

ORD record: ord-ea0a9ac3c5ae45daa88e2163116b0a6f
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

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