Methanol → HCID 58063582, compound

HRID 2035692Notes

Reaction equation

HRID 2035692 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[S:8][C:9]([CH:12]=O)=[CH:10][N:11]=2)[CH:6]=1.[C:14](=O)([O-])[O-].[K+].[K+].CO>C(Cl)Cl>[C:12]([C:9]1[S:8][C:7]([N:5]2[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]2)=[N:11][CH:10]=1)#[CH:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 77231200HCID 77231200, compound

Product 1

HCID 58063582HCID 58063582, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-bromo-1,3-thiazole-5-carbaldehyde (10 mg, 0.068 mmol), 4-methyl-1H-imidazole (7.23 mg, 0.088 mmol), potassium carbonate (28.1 mg, 0.203 mmol) and DMF (5 ml) were heated at 110° C. for 1 h. The mixture was purified on silica gel (EtOAc/hexane 8:2) to afford 2-(4-methyl-1H-imidazol-1-yl)-1,3-thiazole-5-carbaldehyde (38.4 mg, 0.199 mmol) as a yellow solid. This aldehyde (38.4 mg, 0.199 mmol) and anhydrous potassium carbonate (110 mg, 0.795 mmol) were placed in a 25-ml flask and placed on high vacuum for 10 min. Under N2, anhydrous MeOH (2 ml) was added. To the suspension was added dimethyl (1-diazo-2-oxopropyl) phosphonate (40 μl, 0.256 mmol). The reaction was stirred at rt for 22 h. The mixture was diluted with DCM, washed with water, dried over sodium sulfate, concentrated to afford crude product, which was used in next step directly.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customto afford crude product, which

Sources & evidence

ORD record
ord-5988114849ca46f88da5883e3f5c9ffd
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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