Potassium Carbonate → 2-(7-iodo-6-oxo-8-phenylpyrano[3,2-g]indazol-1(6H)-yl)acetonitrile

HRID 1037412Notes

Reaction equation

HRID 1037412 reaction equation
[I:1][C:2]1[C:3](=[O:21])[C:4]2[C:12]([O:13][C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[C:11]1[C:7]([CH:8]=[N:9][NH:10]1)=[CH:6][CH:5]=2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]#[N:31]>CN(C=O)C>[I:1][C:2]1[C:3](=[O:21])[C:4]2[C:12]([O:13][C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[C:11]1[C:7]([CH:8]=[N:9][N:10]1[CH2:29][C:30]#[N:31])=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 670677727-Iodo-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one

Product 1

HCID 682275892-(7-iodo-6-oxo-8-phenylpyrano[3,2-g]indazol-1(6H)-yl)acetonitrileYield 30.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-iodo-8-phenylpyrano[3,2-g]indazol-6(1H)-one (350 mg, 0.903 mmol) in DMF (10 mL) was added potassium carbonate (415 mg, 3 mmol) and the reaction stirred at RT. After 5 minutes, bromoacetonitrile (162 mg, 1.353 mmol) was added and the reaction stirred at RT for 2 h. The reaction mixture was partitioned between EtOAc and water. The resulting biphasic mixture was separated and the aqueous phase was extracted with EtOAc. The combined organic phase was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 70% EtOAc in cyclohexane) to afford the title compound (116 mg, 30%), 1H NMR (500 MHz, CDCl3): δ 8.18 (br s, 1H), 8.06 (d, J=8.6 Hz, 1H), 7.90-7.88 (m, 2H), 7.75 (d, J=8.3 Hz, 1H), 7.64-7.60 (m, 3H), 5.52 (s, 2H). LCMS (Method J) RT=1.29 min, [M+H]+=428.

Workup

  1. stirringthe reaction stirred at RT for 2 h
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. customThe resulting biphasic mixture was separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organic phase was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e7da796f4244b6596e4ec2aca52360c
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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