Diisopropylethylamine → 2,6-difluoro-N-(5-(2-methylbenzofuran-3-yl)pyridin-2-yl)benzamide

HRID 874679노트

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HRID 874679 반응식
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].[CH3:12][C:13]1[O:14][C:15]2[CH:28]=[CH:27][CH:26]=[CH:25][C:16]=2[C:17]=1[C:18]1[CH:19]=[CH:20][C:21]([NH2:24])=[N:22][CH:23]=1.CCN(C(C)C)C(C)C>ClCCl.O1CCCC1.CO.[OH-].[Na+]>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([NH:24][C:21]1[CH:20]=[CH:19][C:18]([C:17]2[C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=3[O:14][C:13]=2[CH3:12])=[CH:23][N:22]=1)=[O:5]

참가 물질

8

반응물 3

HCID 81531DiisopropylethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 58486878HCID 58486878, 화합물

생성물 1

HCID 584872752,6-difluoro-N-(5-(2-methylbenzofuran-3-yl)pyridin-2-yl)benzamide수율 97.4%

시약·촉매·용매 4

HCID 887Methanol용매HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매

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온도
60 °C

실험 절차

Under an atmosphere of argon, 2,6-difluorobenzoyl chloride (47 mg, 0.3 mmol) was added to a stirred solution of 245 (30 mg, 0.1 mmol) and Hünig's base (140 μL, 104 mg, 0.8 mmol) in dichloromethane (1.0 mL) at room temperature. The reaction was stirred for 0.5 h. The solution was diluted with tetrahydrofuran (0.8 mL), methanol (0.6 mL) and 2 M sodium hydroxide solution (0.2 mL). The mixture was stirred and heated to 60° C. for 15 min then cooled to room temperature, diluted with dichloromethane (10 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-20% ethyl acetate in hexane) provided 246 (35.5 mg, 73%) as a solid: LRESIMS m/z 365.1 [M+H]+, calcd. for C21H15F2N2O2 365.1.

후처리

  1. stirringThe mixture was stirred
  2. temperaturethen cooled to room temperature
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-37c35f3c81da4e1eac0b01a5d64f5c16
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980629B2

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