Dimethylformamide → N-phenyl-4-methoxy-6-{3-(trifluoromethoxy)phenoxy}-2-pyridine carboxamide

HRID 1250480Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[H-].[Na+].Br[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18](Br)[N:17]=1.[CH3:25][N:26]([CH:28]=[O:29])C>CCCCCC>[C:25]1([NH:26][C:28]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:11])([F:12])[F:1])[CH:5]=3)[N:17]=2)=[O:29])[CH:6]=[CH:5][CH:4]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 110 °C

Procedure

2.00 g (0.00937×1.2 mol) of 3-(trifluoromethoxy) phenol was dissolved in about 20 ml of DMF. The solution was further mixed with 0.39 g (ca. 60% in mineral oil; 0.00937×1.04 mol) of NaH and then with 2.50 g (0.00937 mol) of 2,6-dibromo-4-methoxy pyridine. After stirring at about 110° C. for about 4 hours, the obtained mixture was allowed to stand for cooling to room temperature. After the reaction solution was distributed in hexane-saturated sodium bicarbonate water, the organic phase of the obtained solution was washed with saturated brine and dried with anhydrous sodium sulfate. The resultant solution was concentrated and then purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), and the obtained eluate was subjected to recrystallization using hexane, thereby obtaining an aimed product.

Workup

temperaturefor cooling to room temperature
washthe organic phase of the obtained solution was washed with saturated brine
dry with materialdried with anhydrous sodium sulfate
concentrationThe resultant solution was concentrated
custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)
customthe obtained eluate was subjected to recrystallization

Sources & evidence

ORD record: ord-f679f1a0be3743e791a0679138d9e2cb
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06339045B1

Reaction notes

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