Cesium carbonate → 4H-Benzo[b]imidazo[1,2-d][1,4]oxazine-7-carbaldehyde

HRID 2035689Notes

Reaction equation

HRID 2035689 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1I)[CH:11]=[O:12].C(=O)([O-])[O-].[Cs+].[Cs+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.CN(C=O)C>[CH:4]1[N:3]2[C:2]([CH2:6][O:7][C:8]3[CH:9]=[C:10]([CH:11]=[O:12])[CH:13]=[CH:14][C:15]=32)=[N:1][CH:5]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 866614633-(1H-imidazol-2-ylmethoxy)-4-iodobenzaldehyde

Product 1

HCID 866614644H-Benzo[b]imidazo[1,2-d][1,4]oxazine-7-carbaldehydeYield 31.9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a vial, were added copper(I) iodide (27.8 mg, 0.146 mmol), 3-(1H-imidazol-2-ylmethoxy)-4-iodobenzaldehyde (127.7 mg, 0.389 mmol), cesium carbonate (267 mg, 0.819 mmol) and a stir bar. The reaction vial was purged with Argon 3 times. The (R,R)-(−)-N,N′-dimethyl-1,2-cyclohexanediamine (50 mg, 0.352 mmol) and DMF (2 ml) were added. The mixture was heated at 110° C. for 1 h. LCMS showed product formation. The mixture was filtered and purified on reverse phase HPLC to afford desired product (24.8 mg, 0.124 mmol, 31.8% yield).

Workup

  1. customThe reaction
  2. customvial was purged with Argon 3 times
  3. filtrationThe mixture was filtered
  4. custompurified on reverse phase HPLC

Sources & evidence

ORD record
ord-dc6fa02a858645b6be5ceb3d29e2da93
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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