PyBroP → HCID 67264405, compound

HRID 1686137Notes

Reaction equation

HRID 1686137 reaction equation
[F:1][CH:2]([F:12])[C:3]1[N:4]=[C:5]([CH3:11])[S:6][C:7]=1[C:8]([OH:10])=O.[CH3:13][Si:14]([CH3:22])([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([NH2:20])[CH3:19].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(#N)C>[F:12][CH:2]([F:1])[C:3]1[N:4]=[C:5]([CH3:11])[S:6][C:7]=1[C:8]([NH:20][CH:18]([CH3:19])[CH2:17][CH2:16][CH2:15][Si:14]([CH3:22])([CH3:21])[CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 2733179PyBroPHCID 167270564-(Difluoromethyl)-2-methyl-1,3-thiazole-5-carboxylic acidHCID 86643790HCID 86643790, compound

Product 1

HCID 67264405HCID 67264405, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 133 mg of 4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxylic acid, 110 mg 5-(trimethylsilyl)pentan-2-amine, 354 mg of PyBroP [bromo-tris-pyrrolidino-phosphonium hexafluorophosphate], and 142 mg N,N′-diisopropylamine in 10 mL acetonitrile was stirred over night at room temperature. Aqueous work-up [extraction with 1.0M NaOH], and silica gel chromatography yielded 130 mg (53%) of a colourless oil.

Workup

  1. extractionAqueous work-up [extraction with 1.0M NaOH], and silica gel chromatography

Sources & evidence

ORD record
ord-d525e5e97cff48fcba8ffcbae0ab3ef9
Source dataset
uspto-grants-2012_04
Patent number
US08148538B2

Reaction notes

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