Methyl iodide → 4-(Methanesulfonyl-methyl-amino)-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29292Notes

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][S:17]([CH3:20])(=[O:19])=[O:18])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[C:21]([O-])([O-])=O.[K+].[K+].IC>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]([S:17]([CH3:20])(=[O:18])=[O:19])[CH3:21])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of the product of Example 36, Step 1, 4-methanesulfonylamino-3-methyl-benzofuran-2-carboxylic acid ethyl ester (438 mg, 1.47 mmol, 1 eq) and K2CO3 (430 mg, 3.11 mmol, 2.1 eq) in 4 mL of DMF under nitrogen was added 0.18 mL of iodomethane (2.89 mmol, 2 eq). The reaction mixture was sealed and heated to 80° C. for 18 h. After cooling to room temperature and work up, 4-(methanesulfonyl-methyl-amino)-3-methyl-benzofuran-2-carboxylic acid ethyl ester was obtained in pure form without further purification (100% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.4 (t, J=7.1 Hz, 3 H) 2.8 (s, 3 H) 3.0 (s, 3 H) 3.4 (s, 3 H) 4.5 (q, J=7.1 Hz, 2 H) 7.2 (dd, J=7.6, 0.8 Hz, 1 H) 7.4 (m, 1 H) 7.6 (m, 1 H).

Workup

customThe reaction mixture was sealed
temperatureAfter cooling to room temperature

Sources & evidence

ORD record: ord-147deb408b22414ea395fbc427882b3e
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420001B2

Reaction notes

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