2-Bromothiazole → HCID 68579940, compound

HRID 2234051Notes

Reaction equation

HRID 2234051 reaction equation
Cl.[Cl:2][C:3]1[C:7]([Cl:8])=[C:6]([CH3:9])[NH:5][C:4]=1[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11].Br[C:20]1[S:21][CH:22]=[CH:23][N:24]=1.C(N(CC)C(C)C)(C)C>CN1C(=O)CCC1.CCOC(C)=O>[Cl:2][C:3]1[C:7]([Cl:8])=[C:6]([CH3:9])[NH:5][C:4]=1[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)[CH2:15][CH2:14]1)=[O:11]

Participants

6

Reactant 3

HCID 764302-BromothiazoleHCID 81531DiisopropylethylamineHCID 68579996HCID 68579996, compound2×

Product 1

HCID 68579940HCID 68579940, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3,4-Dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide hydrochloride (Intermediate 1; 1 g, 3.2 mmol) was dissolved in NMP (10 ml). Bromothiazole (2.65 g; 16 mmol) was added followed by the addition of N,N-diisopropylethylamine (2.75 ml, 16 mmol). Using a Smith Microwave Synthesizer, the mixture was subjected to single-mode microwave at 150° C. for a total of 3 h. The mixture was diluted with EtOAc and washed well with water, NaHCO3, brine. The organic phase was dried over Na2SO4 and concentrated in vacuo to give the title compound as a brown solid (692 mg).

Workup

  1. customat 150° C.
  2. customfor a total of 3 h
  3. washwashed well with water, NaHCO3, brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-225ef72039bf42d89a5c9b43280b8754
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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