(2,4-Dichlorophenyl)-[3-methyl-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-benzofuran-2-yl]-methanone → N-{6-[2-(2,4-dichloro-benzoyl)-3-methyl-benzofuran-6-yl]-pyridin-2-ylmethyl}-acetamide

HRID 1443365Notes

Reaction equation

HRID 1443365 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[O:12][C:13]2[CH:20]=[C:19](B3OC(C)(C)C(C)(C)O3)[CH:18]=[CH:17][C:14]=2[C:15]=1[CH3:16])=[O:10].Br[C:31]1[N:36]=[C:35]([CH2:37][NH:38][C:39](=[O:41])[CH3:40])[CH:34]=[CH:33][CH:32]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[O:12][C:13]2[CH:20]=[C:19]([C:31]3[N:36]=[C:35]([CH2:37][NH:38][C:39](=[O:41])[CH3:40])[CH:34]=[CH:33][CH:32]=3)[CH:18]=[CH:17][C:14]=2[C:15]=1[CH3:16])=[O:10]

Participants

3

Reactant 2

HCID 59788883(2,4-Dichlorophenyl)-[3-methyl-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-benzofuran-2-yl]-methanoneHCID 59788950N-(6-Bromo-pyridin-2-ylmethyl)acetamide

Product 1

HCID 59788906N-{6-[2-(2,4-dichloro-benzoyl)-3-methyl-benzofuran-6-yl]-pyridin-2-ylmethyl}-acetamide

Procedure

N-{6-[2-(2,4-dichloro-benzoyl)-3-methyl-benzofuran-6-yl]-pyridin-2-ylmethyl}-acetamide was prepared via a Suzuki coupling of ((2,4-dichlorophenyl)-[3-methyl-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-benzofuran-2-yl]-methanone and N-(6-Bromo-pyridin-2-ylmethyl)-acetamide as described in method 6 step 2. 1H-NMR (CD3OD) δ 8.19 (s, 1H), 8.05 (dd, J=9 Hz, J=2 Hz, 1H), 7.99-7.89 (m, 3H), 7.64 (d, J=2 Hz, 1H), 7.57-7.51 (m, 2H), 7.40 (d, J=7 Hz, 1H), 4.59 (s, 2H), 2.62 (s, 3H), 2.07 (s, 3H).

Sources & evidence

ORD record
ord-51ebbc1be3ef4b12a9ed634f7427346f
Source dataset
uspto-grants-2010_02
Patent number
US07659412B2

Reaction notes

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