Methyl 2-bromothiazole-5-carboxylate → HCID 68581194, compound

HRID 2234048Notes

Reaction equation

HRID 2234048 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][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][N:24]=1>CN1C(=O)CCC1>[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][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][N:24]=2)[CH2:15][CH2:14]1)=[O:11]

Participants

4

Reactant 2

HCID 2773502Methyl 2-bromothiazole-5-carboxylateHCID 68579996HCID 68579996, compound2×

Product 1

HCID 68581194HCID 68581194, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3,4-Dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide hydrochloride (Intermediate 1, 0.300 g, 0.961 mmol) was dissolved in NMP (3 ml). TEA (267 μl, 1.922 mmol) was added followed by the addition of methyl 2-bromo-1,3-thiazole-5-carboxylate (0.213 g, 0.961 mmol) at room temperature. Using a Smith Microwave Synthesizer, the mixture was subjected to single-mode microwave at 150° C. for 20 minutes and was partitioned between water and EtOAc. The organic layer was washed with water and combined organic phase was dried over magnesium sulfate and concentrated to give the desired product. (432 mg).

Workup

  1. customat 150° C.
  2. customfor 20 minutes
  3. customwas partitioned between water and EtOAc
  4. washThe organic layer was washed with water and combined organic phase
  5. dry with materialwas dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6649bcc580e948b2a6f3315f19b45c0b
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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