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

HRID 2290126Notes

Reaction equation

HRID 2290126 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:27](=O)([O-])[O-].[K+].[K+].IC>CN(C)C(=O)C>[CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH3:27])[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

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 154540854-[(3,3-Dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester2×

Product 1

HCID 154540914-[Methyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following general procedure F and using 4-[(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 17, 0.043 g, 0.127 mmol), potassium carbonate (0.139 g, 1 mmol) and iodomethane (0.144 g, 1 mmol) in 1 mL of anhydrous N,N-dimethylacetamide, the title compound (0.031 g, 70%) was obtained as a pale yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.78 (d, 2H, J=9.0 Hz), 6.77 (d, 1H, J=2.1 Hz), 6.70 (d, 1H, J=2.1 Hz), 6.55 (d, 2H, J=9.0 Hz), 4.24 (q, 2H, J=7.1 Hz), 4.20 (s, 2H), 3.24 (s, 3H), 3.01 (heptet, 1H, J=7.0 Hz), 1.28 (t, 3H, J=7.1 Hz), 1.25 (s, 6H), 1.15 (d, 6H, J=7.0 Hz).

Sources & evidence

ORD record
ord-6aa3f54883654231958dbccdb1098a77
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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