Methyl iodide → HCID 86671042, compound

HRID 1037316Notes

Reaction equation

HRID 1037316 reaction equation
[I:1][C:2]1[C:3](=[O:22])[C:4]2[CH:5]=[CH:6][N:7]3[C:20](=[O:21])[NH:19][N:18]=[C:8]3[C:9]=2[O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:23](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[I:1][C:2]1[C:3](=[O:22])[C:4]2[CH:5]=[CH:6][N:7]3[C:20](=[O:21])[N:19]([CH3:23])[N:18]=[C:8]3[C:9]=2[O:10][C:11]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86671041HCID 86671041, compound

Product 1

HCID 86671042HCID 86671042, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled solution of 7-iodo-8-phenyl-2H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalene-3,6-dione in DMF (2 mL) was added cesium carbonate (73 mg, 0.224 mmol) and iodomethane (0.021 mL, 0.336 mmol). The mixture was allowed to warm to RT and stirred for 1.5 hours. The reaction mixture was partitioned between EtOAc and water. The aqueous phase was isolated and extracted twice with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to give the title compound (25.5 mg, 51%, over 2 steps) as a yellow solid. LCMS (Method A): RT=3.98 min, [M+H]+=420.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. customThe aqueous phase was isolated
  3. extractionextracted twice with EtOAc
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0d69fc8879347b3b85279980f0b1d99
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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