Methyl iodide → HCID 15454090, compound

HRID 2290125Notes

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(=O)([O-])[O-].[K+].[K+].IC.CN(C)[C:36](=O)[CH3:37]>>[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH2:36][CH3:37])[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

Reactant 4

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 31374Dimethylacetamide

HCID 15454084HCID 15454084, compound2×

Product 1

HCID 15454090HCID 15454090, compoundYield 68%

Procedure

Following general procedure G and using 4-[(3,3-dimethyl-7-ethyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 16, 0.18 g, 0.53 mmol), potassium carbonate (0.73 g, 5.3 mmol) and iodomethane (0.83 g, 5.3 mmol) in 2 mL of anhydrous N,N-dimethylacetamide, the title compound (0.134 g, 68%) was obtained as a pale yellow oil. The reaction was performed in a sealed tube. 1H NMR (300 MHz, CDCl3): δ 7.82 (d, 2H, J=9.0 Hz), 6.79 (d, 1H, J=2.0 Hz), 6.76 (d, 1H, J=2.0 Hz), 6.57 (d, 2H, J=9.0 Hz), 4.31 (q, 2H, J=7.1 Hz), 4.27 (s, 2H), 3.72 (q, 2H, J=7.1 Hz), 2.60 (q, 2H J=7.6 Hz), 1.35 (t, 3H, J=7.1 Hz), 1.33 (s, 6H), 1.26-1.19 (m, 6H).

Sources & evidence

ORD record: ord-f299d049756b4b249acd444102b43a0c
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093838

Reaction notes

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