2-(Tributylstannyl)pyrimidine → 4-(4-Pyrimidin-2-yl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1157179

반응식

HRID 1157179 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:27]1[N:32]=[CH:31][CH:30]=[CH:29][N:28]=1)CCC>COCCOC.CCOC(C)=O.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:27]3[N:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 2

HCID 27632512-(Tributylstannyl)pyrimidineHCID 11210451Tert-butyl 4-((4-bromophenyl)amino)piperidine-1-carboxylate

생성물 1

HCID 589851534-(4-Pyrimidin-2-yl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 4

HCID 13169693Triphenylphosphine palladium dichloride촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-(4-Bromo-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (355 mg; 1.002 mmol); 2-tributylstannanyl-pyrimidine (1.1 g; 2.98 mmol); triphenylphosphine palladium dichloride (35 mg, 0.049 mmol) was stirred in DME (4 ml) at 100° C. overnight. Reaction mixture was cooled to room temperature, diluted with EtOAc (100 ml) and water (50 ml). Separated organic layer, washed with brine, dried over Na2SO4, then chromatographed on silica gel eluting with 70% v/v EtOAc/Hexanes yielding product at solid (110 mg; 31%)

후처리

  1. customReaction mixture
  2. washSeparated organic layer, washed with brine
  3. dry with materialdried over Na2SO4
  4. customchromatographed on silica gel eluting with 70% v/v EtOAc/Hexanes yielding product at solid (110 mg; 31%)

출처 및 근거

ORD 기록
ord-e64e5671e6d8479f8d65628f7c062c9c
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807672B2

연결된 노트

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