Methyl iodide → HCID 66998280, compound

HRID 559203Notes

Reaction equation

HRID 559203 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:28](=[O:29])[N:27]([CH3:30])[C:11]3[N:12]([CH3:26])[C:13]4[C:18]([C:10]=3[CH:9]=2)=[CH:17][C:16]([C:19]2[S:20][CH:21]=[C:22]([CH2:24][OH:25])[N:23]=2)=[CH:15][CH:14]=4)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:33]1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1.IC.C([O-])(O)=O.[Na+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:28](=[O:29])[N:27]([CH3:30])[C:11]3[N:12]([CH3:26])[C:13]4[C:18]([C:10]=3[CH:9]=2)=[CH:17][C:16]([C:19]2[S:20][CH:21]=[C:22]([CH2:24][O:25][CH3:33])[N:23]=2)=[CH:15][CH:14]=4)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 26541Dibenzo-18-crown-6HCID 516892Sodium BicarbonateHCID 66998365HCID 66998365, compound2×

Product 1

HCID 66998280HCID 66998280, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

120 mg (0.286 mmol) of compound from Example 100 above, 3-(4-fluorophenyl)-6-(4-hydroxymethylthiazol-2-yl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one, are dissolved in 3 ml of DMF. 17 mg (0.429 mmol) of 60% NaH and a spatula of dibenzo-18-crown-6 are added. After stirring for 5 minutes, 27 μl (0.429 mmol) of iodomethane are added. The mixture is allowed to stir for 4 h at ambient temperature. A saturated NaHCO3 solution is added, the mixture is extracted with EtOAc and then with CH2Cl2 and the organic phase is concentrated to dryness without drying. The residue is taken up in MeOH, and the white precipitate is filtered off and washed with MeOH and then with a minimum amount of Et2O.

Workup

  1. stirringto stir for 4 h at ambient temperature
  2. extractionthe mixture is extracted with EtOAc
  3. concentrationwith CH2Cl2 and the organic phase is concentrated to dryness
  4. customwithout drying
  5. filtrationthe white precipitate is filtered off
  6. washwashed with MeOH

Sources & evidence

ORD record
ord-cdd0289e8d7c426e8af003f1fe662b25
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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