Dichloromethane → 5-[2-(1-Hydroxy-1-methyl-ethyl)-pyridin-4-yloxy]-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide

HRID 45110

반응식

HRID 45110 반응식
C[Mg]I.C(OC([C:11]1[CH:16]=[C:15]([O:17][C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[N:23]([C:27](=[O:39])[NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)[CH:22]=[CH:21]3)[CH:14]=[CH:13][N:12]=1)=O)(C)(C)C.C(Cl)Cl>C1COCC1.CO>[F:36][C:35]([F:38])([F:37])[C:31]1[CH:30]=[C:29]([NH:28][C:27]([N:23]2[C:24]3[C:20](=[CH:19][C:18]([O:17][C:15]4[CH:14]=[CH:13][N:12]=[C:11]([C:15]([OH:17])([CH3:16])[CH3:14])[CH:16]=4)=[CH:26][CH:25]=3)[CH:21]=[CH:22]2)=[O:39])[CH:34]=[CH:33][CH:32]=1

참가 물질

6

반응물 3

HCID 6344DichloromethaneHCID 593947604-[1-(3-Trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-pyridine-2-carboxylic acid tert-butyl esterHCID 178418373HCID 178418373, 화합물

생성물 1

HCID 674332485-[2-(1-Hydroxy-1-methyl-ethyl)-pyridin-4-yloxy]-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

Methyl magnesium iodide (0.30 mL, 3.0 M) is added to a solution of 4-[1-(3-Trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-pyridine-2-carboxylic acid tert-butyl ester (0.150 g, 0.302 mmol) in THF (5 mL) at rt. After stirring overnight the reaction is diluted with MeOH (5 mL) and workup done with DCM and pH 7 buffer. Following concentration the residue is separated by FCC (80-100% EtOAc/heptane) to give the title compound. MS (ESI) m/z 456.1 (M+1).

후처리

  1. concentrationconcentration the residue
  2. customis separated by FCC (80-100% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-2e0f23df98174bc4bfc0f372bb44b714
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541432B2

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