Isobutylamine → 6Methoxy-2-methyl-benzofuran-3-carboxylic acid isobutyl-amide

HRID 985295Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[CH:7]=[C:8]([CH3:10])[O:9][C:5]=2[CH:4]=1.[C:13](Cl)(=[O:17])C(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].[CH2:23]([NH2:27])[CH:24]([CH3:26])[CH3:25]>>[CH2:23]([NH:27][C:13]([C:7]1[C:6]2[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[O:9][C:8]=1[CH3:10])=[O:17])[CH:24]([CH3:26])[CH3:25]

Participants

Reactant 4

HCID 6558Isobutylamine

HCID 65578Oxalyl chloride

HCID 6451240Aluminum(III) Chloride

HCID 130130736-Methoxy-2-methylbenzofuran

Product 1

HCID 207679286Methoxy-2-methyl-benzofuran-3-carboxylic acid isobutyl-amideYield 73%

Procedure

This material was prepared from 6-methoxy-2-methylbenzofuran 12a (500 mg, 3.1 mmole) by acylation with oxalyl chloride in the presence of AlCl3, followed by treatment with isobutylamine in a manner as previously described for example 1c to give 585 mg (73%) of an off-white solid. 1H NMR (DMSO-d6) δ7.95 (1H, t, J 5.8 Hz), 7.56 (1H, d, J=8.6 Hz), 7.15(1H, d, J=2.3 Hz), 6.91 (1H, dd, J=8.6, 2.3 Hz), 3.76 (3H, s), 3.07 (2H, m), 2.57 (3H, s), 1.83 (1H, m), 0.88 (6H, d, J=6.8 Hz).

Sources & evidence

ORD record: ord-6287ee1603e5425eb8f407ef7c92dd2c
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869962B2

Reaction notes

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