Methyl 4-iodobenzoate → HCID 25159790, compound

HRID 1452742Notes

Reaction equation

I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:23])[CH3:22])#[CH:13]>>[C:21]([N:20]1[C:15]2[C:14](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[C:13]1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1)(=[O:23])[CH3:22]

Participants

Reactant 2

HCID 69273Methyl 4-iodobenzoate

HCID 10261360N-(2-ethynylphenyl)acetamide

Product 1

HCID 25159790HCID 25159790, compoundYield 59%

Procedure

The general procedure was used to convert methyl 4-iodobenzoate and N-(2-ethynylphenyl)acetamide to the title product. Purification by flash chromatography gave the analytically pure product as a white solid, 59% yield. 1H NMR (300 MHz, DMSO) δ 8.20-8.17 (d, J=8.2, 1H), 8.06-8.04 (d, J=8.2, 2H), 7.70-7.67 (d, J=8.3, 2H), 7.66-7.64 (d, J=7.7, 1H), 7.41-7.28 (m, 2H), 6.91 (s, 1H), 3.89 (s, 3H), 2.20 (s, 3H). 13C NMR (75 MHz, DMSO) δ 171.63, 166.71, 139.56, 139.00, 138.06, 130.21, 129.96, 129.78, 129.56, 126.06, 124.37, 124.33, 121.81, 116.10, 113.06, 53.12, 28.53. Anal. Calcd. for C18H15NO3: C, 73.71; H, 5.15; N, 4.78. Found C, 73.50; H, 5.21; N, 4.54.

Sources & evidence

ORD record: ord-5802d14b0a214be9afc995102916fdcb
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473786B1

Reaction notes

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