Methanol → HCID 57562673, compound

HRID 1725457Notes

Reaction equation

HRID 1725457 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:23][OH:24].[C]=O.CN(C)[CH:29]=[O:30]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[S:10]1[CH:11]=[CH:12][N:13]=[C:9]1[NH:8][C:6]1[N:7]=[C:2]([C:23]([O:30][CH3:29])=[O:24])[CH:3]=[CH:4][CH:5]=1

Participants

8

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 57562594HCID 57562594, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 57562673HCID 57562673, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Procedure

A mixture of 1.94 g (9.17 mmol) of (6-chloro-pyridin-2-yl)-thiazol-2-yl-amine, 206 mg (0.918 mmol) of palladium acetate, 508 mg (0.916 mmol) of 1,1′-bisdiphenylphosphinoferrocene, 2.40 ml (13.8 mmol) of N,N-diisopropylethylamine, 10 ml of methanol and 15 ml of N,N-dimethylformamide was stirred at 100° C. for 3 hours and 15 minutes under 3 atmospheric pressure of carbon monoxide and cooled on an ice bath. The resulting solid was filtered and washed with ether to give 1.53 g (6.50 mmol) of the title compound as a light brown solid.

Workup

  1. temperaturecooled on an ice bath
  2. filtrationThe resulting solid was filtered
  3. washwashed with ether

Sources & evidence

ORD record
ord-20e9411ea3a74df9a5b3ea887df88838
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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