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

HRID 29312

Reaction equation

HRID 29312 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([OH:12])=O.[CH3:13][C:14]1([CH3:28])[C:18]([CH3:20])([CH3:19])[O:17][B:16]([C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)[O:15]1>>[CH3:19][C:18]1([CH3:20])[C:14]([CH3:13])([CH3:28])[O:15][B:16]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:10]([C:2]3[O:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[CH:3]=3)=[O:12])=[CH:23][CH:22]=2)[O:17]1

Participants

3

Reactant 2

HCID 10331Benzofuran-2-carboxylic acidHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 66996737Benzofuran-2-carboxylic acid [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amideYield 83%

Procedure

Amide coupling of benzofuran-2-carboxylic acid with 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine was done according to Example 20, Step 4 to give benzofuran-2-carboxylic acid [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amide in 83% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.3 (s, 12 H) 7.4 (m, 1 H) 7.5 (m, 1 H) 7.7 (d, J=8.3 Hz, 2 H) 7.7 (dd, J=8.5, 0.9 Hz, 1 H) 7.8 (m, 4 H) 10.6 (s, 1 H)

Sources & evidence

ORD record
ord-27a217f1dcb3412ea82ee388290e69b1
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Linked notes

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