Methyl iodide → HCID 11502499, compound

HRID 1686041Notes

Reaction equation

HRID 1686041 reaction equation
[H-].[Na+].[CH2:3]([C:10]1[C:14]2[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[N:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]=1[CH3:28])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH3:30]>CN(C)C=O.C(OCC)(=O)C>[ClH:27].[CH2:3]([C:10]1[C:14]2[C:15]([O:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)=[N:16][CH:17]=[CH:18][C:13]=2[N:12]([CH3:30])[C:11]=1[CH3:28])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11524133HCID 11524133, compound

Product 1

HCID 11502499HCID 11502499, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (30 mg, 0.066 mmol) prepared in Example 77 was treated with a saturated sodium bicarbonate solution to obtain 3-benzyl-2-methyl-4-(4-chlorobenzyloxy)-1H-pyrrolo[3,2-c]pyridine (24 mg, 0.065 mmol). Sodium hydride (60%, 4.9 mg, 0.118 mmol) was added at room temperature to a solution of 3-benzyl-2-methyl-4-(4-chlorobenzyloxy)-1H-pyrrolo[3,2-c]pyridine (24 mg, 0.065 mmol) in N,N-dimethylformamide (1 ml) and then the reaction mixture was stirred for 30 minutes. Iodomethane (0.007 ml, 0.118 mmol) was added to the reaction mixture, which was then stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate (10 ml) and washed with water (10 ml) three times. The organic layer was separated, dried on anhydrous magnesium sulfate, and then concentrated. The resulting residue was dissolved in ethyl acetate (1 ml), saturated with hydrochloric acid gas, and then filtered to give the titled compound as a white solid. (Yield: 57.1%)

Workup

  1. stirringwas then stirred for 1 hour at room temperature
  2. washwashed with water (10 ml) three times
  3. customThe organic layer was separated
  4. dry with materialdried on anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. dissolutionThe resulting residue was dissolved in ethyl acetate (1 ml), saturated with hydrochloric acid gas
  7. filtrationfiltered

Sources & evidence

ORD record
ord-006c3a9057b440bc9ee51c4e2526dca7
Source dataset
uspto-grants-2012_04
Patent number
US08148529B2

Reaction notes

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