4-(Trifluoromethyl)aniline → HCID 57857493, 화합물

HRID 2266966노트

반응식

HRID 2266966 반응식
CS(O[C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])(=O)=O.[F:17][C:18]([F:27])([F:26])[C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CC(O)(C)C>[F:17][C:18]([F:26])([F:27])[C:19]1[CH:20]=[CH:21][C:22]([NH:23][C:6]2[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 99644-(Trifluoromethyl)anilineHCID 11430Potassium CarbonateHCID 57857516HCID 57857516, 화합물

생성물 1

HCID 57857493HCID 57857493, 화합물수율 93.1%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

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온도
110 °C

실험 절차

Following general procedure A, a mixture of ethyl 3-(methylsulfonyloxy)benzoate (122 mg, 0.5 mmol), 4-(trifluoromethyl)aniline (75 μL, 0.6 mmol), K2CO3 (97 mg, 0.7 mmol), 10 (4 mg, 1 mol %), 1 (2.5 mg, 1 mol %), and t-BuOH (6 mL) was heated to 110° C. for 16 h. The crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-30% EtOAc/hexanes) to provide the title compound as a white solid (144 mg, 93%), mp 106-108° C. 1H NMR (300 MHz, CDCl3) δ: 7.81 (s, 1H), 7.71 (d, J=7.0 Hz, 1H), 7.49 (d, J=8.5 Hz, 2H), 7.36 (m, 2H), 7.07 (d, J=8.5 Hz, 2H), 6.13 (s 1H), 4.38 (q, J=7.0 Hz, 2H), 1.39 (t, J=7.0 Hz, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 166.7, 146.3, 141.8, 132.1, 130.1, 129.8, 127.1, 127.0, 127.0, 126.9, 126.6, 123.8, 123.8, 123.0, 122.6, 122.2, 120.6, 116.0, 61.5, 14.5 ppm. IR (neat, cm−1): 3358, 1701, 1620, 1543, 1333, 1158, 1108, 1070, 751. Anal. Calcd. for C16H14F3O2N: C, 62.13; H, 4.56. Found: C, 61.97; H, 4.46.

후처리

  1. customThe crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-30% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-1a957fcd923546c68df2f763f6bada51
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858784B2

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