Methyl iodide → HCID 78426555, compound

HRID 2205213Notes

Reaction equation

HRID 2205213 reaction equation
[CH3:1][O:2][C:3]1[C:31]([O:32][CH3:33])=[CH:30][C:6]2[S:7][C:8]([C:10]3[N:14]4[N:15]=[C:16]([NH:19][C:20]5[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=5)[CH:17]=[CH:18][C:13]4=[N:12][CH:11]=3)=[CH:9][C:5]=2[CH:4]=1.[H-].[Na+].I[CH3:37]>CN(C=O)C>[CH3:1][O:2][C:3]1[C:31]([O:32][CH3:33])=[CH:30][C:6]2[S:7][C:8]([C:10]3[N:14]4[N:15]=[C:16]([N:19]([C:20]5[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=5)[CH3:37])[CH:17]=[CH:18][C:13]4=[N:12][CH:11]=3)=[CH:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 90388061HCID 90388061, compound

Product 1

HCID 78426555HCID 78426555, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(5,6-dimethoxybenzo[b]thiophen-2-yl)-N-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-6-amine (50 mg, 0.108 mmol, 1.0 equiv) in DMF (5.0 mL) was added NaH (13 mg, 0.324 mmol, 3.0 equiv) followed by iodomethane (0.07 mL, 0.541 mmol, 5.0 equiv). After 1 h, the reaction was quenched with saturated aqueous solution of ammonium chloride then extracted with ethyl acetate. Purification by column chromatography using 2% methanol in dichloromethane elution gave 30 mg of the brown solid, 58%.

Workup

  1. customthe reaction was quenched with saturated aqueous solution of ammonium chloride
  2. extractionthen extracted with ethyl acetate
  3. customPurification by column chromatography
  4. wash2% methanol in dichloromethane elution

Sources & evidence

ORD record
ord-c08251878d1c4832847d4d591c426f47
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

Loading…