Methanol → 7-ethynyl-4H-imidazo[2,1-c][1,4]benzoxazine

HRID 2035690Notes

Reaction equation

HRID 2035690 reaction equation
[CH:1]1[N:9]2[C:4]([CH2:5][O:6][C:7]3[CH:13]=[C:12]([CH:14]=O)[CH:11]=[CH:10][C:8]=32)=[N:3][CH:2]=1.[C:16](=O)([O-])[O-].[K+].[K+].CO>C(Cl)Cl>[C:14]([C:12]1[CH:11]=[CH:10][C:8]2[N:9]3[CH:1]=[CH:2][N:3]=[C:4]3[CH2:5][O:6][C:7]=2[CH:13]=1)#[CH:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 866614644H-Benzo[b]imidazo[1,2-d][1,4]oxazine-7-carbaldehyde

Product 1

HCID 580636067-ethynyl-4H-imidazo[2,1-c][1,4]benzoxazineYield 43.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4H-Imidazo[2,1-c][1,4]benzoxazine-7-carbaldehyde (44 mg, 0.140 mmol) and anhydrous potassium carbonate (120 mg, 0.868 mmol) were placed in a 25-ml flask and placed on high vacuum for 10 min. Under N2, anhydrous MeOH (5 ml) was added. To the suspension was added dimethyl (1-diazo-2-oxopropyl) phosphonate (0.03 ml, 0.192 mmol). The reaction was stirred at rt for 2 h. The mixture was diluted with DCM, washed with water, dried over sodium sulfate, concentrated to afford desired product (11.9 mg, 0.061 mmol, 43.3% yield).

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4bda9907f1be46018a5c9c67bb03cc76
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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