Water → (4-Chloro-8-trifluoromethyl-quinolin-3-yl)-pyridin-2-yl-methanone

HRID 2104476

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.C(O[C:16]([C:18]1[CH:19]=[N:20][C:21]2[C:26]([C:27]=1[Cl:28])=[CH:25][CH:24]=[CH:23][C:22]=2[C:29]([F:32])([F:31])[F:30])=[O:17])C.O>C1COCC1>[Cl:28][C:27]1[C:26]2[C:21](=[C:22]([C:29]([F:30])([F:31])[F:32])[CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19][C:18]=1[C:16]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)=[O:17]

Participants

Conditions

Temperature: -78 °C

Procedure

2-Bromopyridine (0.74 mL, 7.90 mmol) was taken into THF (30 mL) and cooled to −78° C. Then BuLi (4.8 mL, 7.90 mmol, 1.6 M solution in hexane) was added dropwise and then stirred for 30 minutes. Next, 4-Chloro-8-(trifluoromethyl)-3-quinolinecarboxylic acid ethyl ester (2.0 g, 6.58 mmol) in THF (10 mL) was added rapidly and stirred at −78° C. for 4 hours. The reaction was poured into water/saturated NH4Cl solution and then extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated. The resulting material was purified via column chromatography using 15% ethyl acetate in hexane as the eluent to yield 0.823 g of (4-chloro-8-trifluoromethyl-quinolin-3-yl)-pyridin-2-yl-methanone as a yellow solid.

Workup

stirringstirred at −78° C. for 4 hours
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe resulting material was purified via column chromatography

Sources & evidence

ORD record: ord-1c791553cc134315ab75db10bb4b34e4
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576215B2

Linked notes

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