Hydrochloric Acid → N-Benzyl-N-[2-(5-ethynyl-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide

HRID 554646Notes

Reaction equation

C1CCCCC=1.O1CCCC1.B.[CH2:13]([N:20]([CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[C:35]1[C:36]([O:47][CH3:48])=[N:37][CH:38]=[C:39]([C:41]#[C:42][Si](C)(C)C)[CH:40]=1)[C:21](=[O:23])[CH3:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+].OO.Cl>C1COCC1.CO>[CH2:13]([N:20]([CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:28]=[CH:27][C:26]=1[C:35]1[C:36]([O:47][CH3:48])=[N:37][CH:38]=[C:39]([C:41]#[CH:42])[CH:40]=1)[C:21](=[O:23])[CH3:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To cyclohexene (0.12 mL, 1.14 mmol) in THF (0.3 mL) at 0° C. was added borane tetrahydrofuran complex (1M in THF; 0.53 mL, 0.53 mmol), and the reaction was stirred for 1.5 hours. N-Benzyl-N-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide (0.084 g, 0.15 mmol) in THF (2 mL) was added dropwise, and the reaction was stirred for 1 hour at room temperature. The mixture was cooled to 0° C., and MeOH (0.9 mL) was added, followed by 1N aqueous NaOH (0.53 mL, 0.53 mmol) and hydrogen peroxide (30%; 0.16 mL, 1.55 mmol), and the reaction was stirred for 1 hour at 0° C. and 1.5 hours at 40° C. The mixture was acidified with 1N aqueous HCl and extracted with EtOAc to give N-Benzyl-N-[2-(5-ethynyl-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide.

Workup

stirringthe reaction was stirred for 1 hour at room temperature
stirringthe reaction was stirred for 1 hour at 0° C. and 1.5 hours at 40° C
extractionextracted with EtOAc

Sources & evidence

ORD record: ord-d31ae98f19da455abfb8fe0881b1ff97
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049015B2

Reaction notes

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