Methyl iodide → HCID 11553576, compound

HRID 2059610Notes

Reaction equation

HRID 2059610 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[O:7][C:8]3[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:9]=3[C:10]=2[C:11]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)=[O:12])[N:3]=[CH:2]1.[H-].[Na+].[CH3:33]I>C1COCC1>[CH3:33][N:1]1[CH:5]=[C:4]([C:6]2[O:7][C:8]3[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:9]=3[C:10]=2[C:11]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)=[O:12])[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178487573HCID 178487573, compound

Product 1

HCID 11553576HCID 11553576, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This material was prepared by N-methylation of [2-(1H-Imidazol-4-yl)-6-methoxy-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone (entry 45, Table 1) was made from Il-0085 by N-methylation. 20 mg of starting material (0.049 mmol) was dissolved in 1 ml dry THF then treated with 9 mg of 60% NaH (0.225 mmol) then after 10 minutes with MeI (15 uL, 0.24 mmol) and left over night then quenched with 10% NH4Cl extracted with EtOAc and chromatographed with straight EtOAc to give 12 mg product (58% yield). Proton data is 7.86 (s, 1H), 7.62 (s, 1H), 7.13-7.09 (m, 2H), 7.12 (s, 2H), 6.79 (dd, J=8.7, 2.1 Hz, 1H), 3.92 (s, 3H), 3.84 (s, 3H), 3.76 (s, 6H), 3.72 (s, 3H).

Workup

  1. waitleft over night
  2. customthen quenched with 10% NH4Cl
  3. extractionextracted with EtOAc
  4. customchromatographed with straight EtOAc

Sources & evidence

ORD record
ord-c97ee0867c0c4ea295bece421e8873f7
Source dataset
uspto-grants-2012_10
Patent number
US08278290B2

Reaction notes

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