Methyl iodide → HCID 22054598, compound

HRID 1374773Notes

Reaction equation

HRID 1374773 reaction equation
I[CH3:2].[Cl:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:15][NH:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)=[C:11]([CH3:14])[CH:12]=2)[N:7]=[C:6]([CH3:25])[CH:5]=1>CN(C)C=O>[Cl:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:15][N:16]([CH3:2])[C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)=[C:11]([CH3:14])[CH:12]=2)[N:7]=[C:6]([CH3:25])[CH:5]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 22054608HCID 22054608, compound

Product 1

HCID 22054598HCID 22054598, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Iodomethane (46 mg, 0.33 mmol) was added to a solution of 4-[(4-chloro-2,6-dimethyl-quinolin-7-ylmethyl)-amino]-benzonitrile (example 101b, 70 mg, 0.22 mmol) in N,N-dimethylformamide (1 mL) at 0° C. The reaction mixture was stirred for 1 h at 0° C. and 1 h at r.t., then partitioned between dichloromethane and 1 M aq. sodium hydroxide solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Flash chromatography (SiO2, hexane/ethyl acetate 2:1, then 1:1) afforded the title compound (63 mg, 86%). White solid, ISP-MS: m/e=336.2 ([M+H]+).

Workup

  1. custompartitioned between dichloromethane and 1 M aq. sodium hydroxide solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-b31e64e30e0a4581b79d129daf9e18ff
Source dataset
uspto-grants-2007_01
Patent number
US07166589B2

Reaction notes

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