Methyl iodide → 4-Dimethylcarbamoyl-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29294Notes

Reaction equation

[CH2:1](OC(C1OC2C=CC=C(C(=O)N)C=2C=1C)=O)C.[H-].[Na+].IC.[CH2:23]([O:25][C:26]([C:28]1[O:29][C:30]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38](=[O:41])[NH:39][CH3:40])[C:31]=2[C:32]=1[CH3:33])=[O:27])[CH3:24]>CN(C=O)C>[CH2:23]([O:25][C:26]([C:28]1[O:29][C:30]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38](=[O:41])[N:39]([CH3:1])[CH3:40])[C:31]=2[C:32]=1[CH3:33])=[O:27])[CH3:24]

Participants

Conditions

Temperature: 50 °C

Procedure

To 200 mg of 4-carbamoyl-3-methyl-benzofuran-2-carboxylic acid ethyl ester (0.81 mmol, 1 eq.) in 5 mL of DMF was added 50 mg of NaH (60% in mineral oil, 1.25 mmol, 1.5 eq) under nitrogen. After 30 min of reaction, iodomethane (0.053 mL, 0.85 mmol, 1 eq) was added to the reaction. The mixture was then heated to 50° C. for 12 h. After work up and column chromatography, a mixture of 3-methyl-4-methylcarbamoyl-benzofuran-2-carboxylic acid ethyl ester and 4-dimethylcarbamoyl-3-methyl-benzofuran-2-carboxylic acid ethyl ester was obtained (76 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.3 (t, J=7.1 Hz, 3 H) 2.8 (d, J=4.5 Hz, 6 H) 4.4 (q, J=7.2 Hz, 2 H) 7.3 (dd, J=7.3, 1.0 Hz, 1 H) 7.5 (dd, J=8.3, 7.3 Hz, 1 H) 7.8 (dd, J=8.5, 0.9 Hz, 1 H).

Workup

additionwas added to the reaction

Sources & evidence

ORD record: ord-3fe1978ce5da438cb6fbb1ea6961b99a
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420001B2

Reaction notes

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