Methyl iodide → HCID 68716001, compound

HRID 29299Notes

Reaction equation

HRID 29299 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17](=[O:19])[CH3:18])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].I[CH3:21].[H-].[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([N:16]([C:17](=[O:19])[CH3:18])[CH3:21])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 687125374-Acetylamino-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 68716001HCID 68716001, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-acetylamino-3-methyl-benzofuran-2-carboxylic acid ethyl ester (300 mg, 1.15 mmol, 1 eq, prepared according to Example 48, Step 1) under nitrogen was added 5 mL of DMF, iodomethane (79 uL, 1.26 mmol, 1.1 eq), and sodium hydride (60%, 51 mg, 1.26 mmol, 1.1 eq). The reaction mixture was stirred at room temperature for 4 h. After work up and flash column chromatography (5-40% ethyl acetate/hexanes), 4-(acetyl-methyl-amino)-3-methyl-benzofuran-2-carboxylic acid ethyl ester was obtained in 35% yield (112 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.3 (t, J=7.2 Hz, 3 H) 1.7 (s, 3 H) 2.5 (s, 3 H) 3.2 (s, 3 H) 4.4 (m, 2 H) 7.3 (dd, J=7.6, 0.8 Hz, 1 H) 7.6 (dd, J=8.5, 7.7 Hz, 1 H) 7.8 (dd, J=8.5, 0.9 Hz, 1 H).

Sources & evidence

ORD record
ord-928d608b884945b4956997f1388a4561
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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