Methyl iodide → HCID 68632375, compound

HRID 1809465Notes

Reaction equation

HRID 1809465 reaction equation
[C:1]([O-])([O-])=O.[Cs+].[Cs+].[C:7]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:23]=[C:22]3[C:17]([CH:18]=[CH:19][CH:20]=[C:21]3[C:24]([OH:26])=[O:25])=[N:16]2)=[CH:11][CH:10]=1)#[N:8].IC>CN(C=O)C.CCOC(C)=O>[C:7]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:23]=[C:22]3[C:17]([CH:18]=[CH:19][CH:20]=[C:21]3[C:24]([O:26][CH3:1])=[O:25])=[N:16]2)=[CH:11][CH:10]=1)#[N:8]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 69813108HCID 69813108, compound

Product 1

HCID 68632375HCID 68632375, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cs2CO3 (1.2 eq.) was added to a solution of (C6) in dry DMF (0.2 M). The resulting white suspension was stirred at RT for 30 min. After cooling down to 0° C., iodomethane (7 eq.) was added, then, the reaction mixture was stirred at RT for 90 min. The solution was diluted with EtOAc and washed with brine (2×) and dried (Na2SO4). Evaporation of the solvent afforded the title compound that was used in the next step without further purification. 1H NMR (300 MHz, CDCl3, 300K) δ 9.02 (1H, s), 8.14 (2H, d, J=8.7 Hz), 8.01-7.95 (2H, m), 7.85 (2H, d, J=8.5 Hz), 7.42 (1H, t, J=7.4 Hz), 4.02 (3H, s). MS (ES+) C16H11N3O2 required: 277, found: 278 (M+H)+.

Workup

  1. temperatureAfter cooling down to 0° C.
  2. stirringthe reaction mixture was stirred at RT for 90 min
  3. washwashed with brine (2×)
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-35659962009c46068758b7053e133e30
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

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