Methyl iodide → 4-[Ethyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester

HRID 2290127Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:23]([CH3:25])[CH3:24])[C:15]3[O:19][CH2:18][C:17]([CH3:21])([CH3:20])[C:16]=3[CH:22]=2)=[CH:7][CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].IC.CN(C)[C:37](=O)[CH3:38]>>[CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH2:37][CH3:38])[C:12]2[CH:13]=[C:14]([CH:23]([CH3:25])[CH3:24])[C:15]3[O:19][CH2:18][C:17]([CH3:21])([CH3:20])[C:16]=3[CH:22]=2)=[CH:9][CH:10]=1)[CH3:2]

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 31374Dimethylacetamide

HCID 154540854-[(3,3-Dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester2×

Product 1

HCID 154540924-[Ethyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl esterYield 75%

Procedure

Following general procedure G and using 4-[(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 17, 0.064 g, 0.19 mmol), potassium carbonate (0.105×2 g, 0.76×2 mmol) and iodomethane (0.24×2 g, 0.76×2 mmol) in 2 mL of anhydrous N,N-dimethylacetamide, the title compound (0.05 g, 75%) was obtained as a pale yellow oil. This reaction was performed in a sealed tube for 96 hours, with addition of a second equivalent of potassium carbonate and iodomethane to the reaction mixture after 48 hours. 1H NMR (300 MHz, CDCl3): δ 7.75 (d, 2H, J=9.0 Hz), 6.74 (d, 1H, J=2.1 Hz), 6.67 (d, 1H, J=2.1 Hz), 6.49 (d, 2H, J=9.0 Hz), 4.23 (q, 2H, J=7.1 Hz), 4.20 (s, 2H), 3.66 (q, 2H, J=7.1 Hz), 3.01 (heptet, 1H J=6.8 Hz), 1.27 (t, 3H, J=7.1 Hz), 1.25 (s, 6H), 1.19-1.13 (m, 9H).

Sources & evidence

ORD record: ord-a0baf7110e3a463a93a4f6b7e155307b
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093838

Reaction notes

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