Diisopropylamine → HCID 178488436, compound

HRID 2244586Notes

Reaction equation

[Li:1]CCCC.[CH:6]([NH:9][CH:10]([CH3:12])[CH3:11])([CH3:8])[CH3:7].[CH3:13][C:14]1[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=O.[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=1>C1COCC1>[Li+:1].[CH3:7][CH:6]([N-:9][CH:10]([CH3:12])[CH3:11])[CH3:8].[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([C:33]2[N:34]=[C:16]([OH:18])[C:15]3[CH:19]=[CH:20][C:21]([C:23]([F:26])([F:25])[F:24])=[N:22][C:14]=3[CH:13]=2)=[CH:31][CH:30]=1

Participants

Conditions

Temperature: -40 °C

Procedure

A solution of LDA (2.4 mmol) was prepared by adding n-BuLi (1.7 mL, 2.4 mmol, 1.4 M in hexanes) via syringe to a solution of diisopropylamine (247 mg, 2.4 mmol) in THF (10 mL) at 0° C. and stirring for 15 minutes. The solution was then cooled to −40° C., then 2-methyl-6-trifluoromethylnicotinic acid (250 mg, 1.2 mmol) in THF (5 mL) was added via syringe. After stirring at −40° C. for 30 minutes, 4-methoxybenzonitrile (162 mg, 1.2 mmol) in THF (5 mL) was added via syringe. The reaction mixture was allowed to warm to room temperature and stirred for 16 hours. The reaction was quenched by addition of sat. NH4Cl solution. A precipitate formed which was collected by vacuum filtration giving the title compound (150 mg, 40%) as an off white solid.

Workup

stirringAfter stirring at −40° C. for 30 minutes
temperatureto warm to room temperature
stirringstirred for 16 hours
customThe reaction was quenched by addition of sat. NH4Cl solution
customA precipitate formed which
filtrationwas collected by vacuum filtration

Sources & evidence

ORD record: ord-0e2c59b799e143e498cb05245bdec6f2
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678911B2

Reaction notes

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