Diisopropylethylamine → 2-Fluoro-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-3-trifluoromethyl-benzamide

HRID 877965노트

반응식

HRID 877965 반응식
[F:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:15][NH:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29].CCN(C(C)C)C(C)C>C1COCC1>[F:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:16]([CH3:15])[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])=[O:5]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27375592-Fluoro-3-(trifluoromethyl)benzoyl chlorideHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

생성물 1

HCID 601970952-Fluoro-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-3-trifluoromethyl-benzamide수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-Fluoro-3-trifluoromethylbenzoyl chloride (92 mg, 0.41 mmol, CAS RN 208173-19-7) was added to a solution of methyl-(4-o-tolyl-pyridin-3-yl)-amine (40 mg, 0.20 mmol, example 1, intermediate a) and DIPEA (70 μL, 0.40 mmol) in THF (1 mL). The reaction mixture was stirred overnight, filtered and all volatiles removed. The resulting oil was purified by flash chromatography on silica gel eluting with 33-50% EtOAc in n-hexane to yield the product as a waxy solid (65 mg, 83%). MS (ESI): m/z=470.0 [M+H]+.

후처리

  1. filtrationfiltered
  2. customall volatiles removed
  3. customThe resulting oil was purified by flash chromatography on silica gel eluting with 33-50% EtOAc in n-hexane

출처 및 근거

ORD 기록
ord-cdbdc46a06eb452ab03626406c542c50
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987307B2

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