4-Fluoroaniline → N-(4-Fluorophenyl)-6-[3-(trifluoromethyl)phenoxy]pyrazine-2-carboxamide

HRID 582255

반응식

HRID 582255 반응식
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[N:3]=1.[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.[C:27](=O)([O-])[O-:28].[Na+].[Na+]>C1(C)C(C)=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2[C-](C(P(C(C)(C)C)C(C)(C)C)C)C=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:27]([C:2]2[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=3)[N:3]=2)=[O:28])=[CH:22][CH:21]=1

참가 물질

7

실험 절차

Analogously to Example 3, 25 mmol of 2-chloro-6-[3-(trifluoromethyl)phenoxy]pyrazine (prepared according to U.S. Pat. No. 4,254,125, Example 21), 27.5 mmol of 4-fluoroaniline, 2.92 g (27.5 mmol) of sodium carbonate, 17.5 mg (25 μmol) of dichlorobis(triphenylphosphine)palladium(II) and 0.31 g (0.75 mmol) of (±)-1-[2-(diphenylphosphino)-ferrocenyl]ethyl-di-tert-butylphosphine in 25 ml of xylene were reacted under a CO pressure of 17 bar at 120° C. for 21 hours. The composition of the dissolved products in the xylene phase was determined by GC. 65.3 percent of the title compound (amide) and 34.7 percent of by-product (secondary amine) were found. The amide was isolated by column chromatography and purified. Data concerning the title product was:

출처 및 근거

ORD 기록
ord-6430dfcc27fc4d51822ec38a44870022
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922870

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