5-Bromo-[1,3]thiazolo[5,4-b]pyridin-2-amine → 2-(2,6-Dichlorophenyl)-1H-indole-6-carboxylic acid (5-bromothiazolo[5,4-b]pyridin-2-yl)-amide

HRID 1514947Notes

Reaction equation

HRID 1514947 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([C:18](O)=[O:19])[CH:12]=2.[Br:21][C:22]1[N:27]=[C:26]2[S:28][C:29]([NH2:31])=[N:30][C:25]2=[CH:24][CH:23]=1>>[Br:21][C:22]1[N:27]=[C:26]2[S:28][C:29]([NH:31][C:18]([C:13]3[CH:12]=[C:11]4[C:16]([CH:17]=[C:9]([C:3]5[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=5[Cl:1])[NH:10]4)=[CH:15][CH:14]=3)=[O:19])=[N:30][C:25]2=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 457899775-Bromo-[1,3]thiazolo[5,4-b]pyridin-2-amineHCID 669660532-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid

Product 1

HCID 866512682-(2,6-Dichlorophenyl)-1H-indole-6-carboxylic acid (5-bromothiazolo[5,4-b]pyridin-2-yl)-amide

Procedure

The title compound was prepared from 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid and 5-bromothiazolo[5,4-b]pyridin-2-ylamine (WO 2007041365) analogous to Example 3-11. 1H NMR (DMSO-d6, 400 MHz): δ 13.08 (s, broad, 1H), 12.01 (s, broad, 1H) 8.33 (s, 1H), 8.11 (d, J=8.5 Hz, 1H), 7.86 (dd, J=8.5, 1.5 Hz, 1H), 7.71 (m, 4H), 7.56 (m, 1H), 6.65 (d, J=1.3 Hz, 1H). MS (m/z) 518.9 (M+1), Retention time=1.58 min (Method 10). High Res. MS: theory 516.9292; measured 516.9277.

Sources & evidence

ORD record
ord-c20e111f680541dcbab8d5cc0b72afd5
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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