Methyl iodide → Benzofuran-2-carboxylic acid methyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amide

HRID 29313Notes

Reaction equation

HRID 29313 reaction equation
[CH3:1][C:2]1([CH3:27])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[O:19][C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[CH:22]=3)=[O:17])=[CH:11][CH:10]=2)[O:3]1.[H-].[Na+].I[CH3:31]>CN(C=O)C>[CH3:31][N:15]([C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:27])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1)[C:16]([C:18]1[O:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[CH:22]=1)=[O:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66996737Benzofuran-2-carboxylic acid [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amide

Product 1

HCID 68714120Benzofuran-2-carboxylic acid methyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amideYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzofuran-2-carboxylic acid [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amide (195 mg, 0.54 mmol, 1 eq) in 3.5 mL of DMF under nitrogen atmosphere was added NaH (60% in mineral oil, 23 mg, 0.58 mmol, 1.1 eq). After 30 min of reaction, iodomethane (0.05 mL, 0.8 mmol, 1.5 eq) was added and the reaction was allowed to go for 12 h. After work up and column chromatography, benzofuran-2-carboxylic acid methyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amide (83 mg) was obtained in 41% yield. 1H NMR (400 MHz, Benzene-d6) δ ppm 1.3 (s, 12 H) 3.4 (s, 3 H) 6.9 (d, J=0.8 Hz, 1 H) 7.0 (m, 4 H) 7.2 (m, 2 H) 8.1 (d, J=8.3 Hz, 2 H).

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-342905f765e64017b6c34fd771dd8c18
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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