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

HRID 1157179Notes

Reaction equation

HRID 1157179 reaction equation
[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]

Participants

7

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 13169693Triphenylphosphine palladium dichlorideCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%)

Workup

  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%)

Sources & evidence

ORD record
ord-e64e5671e6d8479f8d65628f7c062c9c
Source dataset
uspto-grants-2010_10
Patent number
US07807672B2

Reaction notes

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