5-Aminoindole → 2-Methyl-6(thieno[3,2-b]pyridin-7-yloxy)-benzofuran-3-carboxylic acid (1H-indol-5-yl)-amide

HRID 985314Notes

Reaction equation

HRID 985314 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:13]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[CH:22][S:23][C:16]=34)[CH:11]=[CH:10][C:5]=2[C:6]=1[C:7](Cl)=[O:8].[NH2:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][CH:29]=[CH:28]2>>[NH:30]1[C:31]2[C:27](=[CH:26][C:25]([NH:24][C:7]([C:6]3[C:5]4[CH:10]=[CH:11][C:12]([O:14][C:15]5[CH:20]=[CH:19][N:18]=[C:17]6[CH:21]=[CH:22][S:23][C:16]=56)=[CH:13][C:4]=4[O:3][C:2]=3[CH3:1])=[O:8])=[CH:33][CH:32]=2)[CH:28]=[CH:29]1

Participants

3

Reactant 2

HCID 788675-AminoindoleHCID 221434802-Methyl-6-[thieno[3,2-b]pyridin-7-yloxy]benzofuran-3-carbonyl chloride

Product 1

HCID 207678882-Methyl-6(thieno[3,2-b]pyridin-7-yloxy)-benzofuran-3-carboxylic acid (1H-indol-5-yl)-amide

Procedure

This material was prepared from 2-methyl-6-[thieno[3,2-b]pyridin-7-yloxy]benzofuran-3-carbonyl chloride 101 and 5-aminoindole in a similar manner as that described for example 108. 1H NMR (DMSO-d6) δ11.04 (1H, s), 9.96 (1H, s), 8.52 (1H, d, J=5.6 Hz), 8.15 (1H, d, J=5.3 Hz), 7.97 (1H, s), 7.83 (1H, d, J=8.3 Hz), 7.69 (1H, d, J=2.3 Hz), 7.60 (1H, d, J=5.6 Hz), 7.36 (2H, s), 7.33 (1H, t, J=2.8 Hz), 7.27 (1H, dd, J=8.6, 2.3 Hz), 6.64 (1H, d, J=5.3 Hz), 6.41 (1H, t, J=2.5 Hz), 2.69 (3H, s).

Sources & evidence

ORD record
ord-ed1cfb48d25c425abe566da472297b48
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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