Methyl iodide → HCID 15454089, compound

HRID 2290124Notes

Reaction equation

HRID 2290124 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:13]=[C:14]([CH2:23][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:26](=O)([O-])[O-].[K+].[K+].IC>CN(C)C(=O)C>[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH3:26])[C:12]2[CH:13]=[C:14]([CH2:23][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 15454084HCID 15454084, compound2×

Product 1

HCID 15454089HCID 15454089, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following general procedure F and using 4-[(3,3-dimethyl-7-ethyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 16, 0.12 g, 0.35 mmol), potassium carbonate (0.49 g, 3.5 mmol) and iodomethane (0.50 g, 3.5 mmol) in 2 mL of anhydrous N,N-dimethylacetamide, the title compound (0.095 g, 80%) was obtained as a pale yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.85 (d, 2H, J=9.1 Hz), 6.81 (d, 1H, J=2.3 Hz), 6.78 (d, 1H, J=2.3 Hz), 6.63 (d, 2H, J=9.1 Hz), 4.31 (q, 2H, J=7.1 Hz), 4.28 (s, 2H), 3.31 (s, 3H), 2.59 (q, 2H,J=7.6 Hz), 1.35 (t, 3H, J=7.1 Hz), 1.33 (s, 6H), 1.22 (t, 3H, J=7.6 Hz).

Sources & evidence

ORD record
ord-8cfa65e902384c1db058ba5a6a3305b8
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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