3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)thiophene-2-carbaldehyde → N-{4-[4-amino-7-(2-formylthien-3-yl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1-methyl-1H-indole-2-carboxamide

HRID 17205

Reaction equation

HRID 17205 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](I)=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:41]2[CH:45]=[CH:44][S:43][C:42]=2[CH:46]=[O:47])O1>>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:41]2[CH:45]=[CH:44][S:43][C:42]=2[CH:46]=[O:47])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 184506733-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)thiophene-2-carbaldehydeHCID 18451298N-[4-(4-amino-7-iodothieno[3,2-c]pyridin-3-yl)-2-methoxyphenyl]-1-methyl-1H-indole-2-carboxamide

Product 1

HCID 18451086N-{4-[4-amino-7-(2-formylthien-3-yl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1-methyl-1H-indole-2-carboxamide

Procedure

N-[4-(4-amino-7-iodothieno[3,2-c]pyridin-3-yl)-2-methoxyphenyl]-1-methyl-1H-indole-2-carboxamide and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde were reacted together according to general procedure A to furnish the title compound. LCMS (Conditions a): MH+=539.0, RT=4.10 minutes; 1H NMR (DMSO-d6, 400 MHz) δ 9.77 (s, 1 H), 9.53 (s, 1 H), 8.29 (d, J=5.3 Hz, 1 H), 7.98 (m, 2 H), 7.63 (m, 6 H), 7.36 (m, 1 H), 7.24 (s, 1 H), 7.15 (m, 1 H), 5.85 (br, 2 H), 4.04 (s, 3 H), 3.92 (s, 3 H).

Sources & evidence

ORD record
ord-20733b77e8fb4fe6b651727a1012a180
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Linked notes

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