1H-Indazol-6-amine → HCID 135988978, compound

HRID 1615292Notes

Reaction equation

HRID 1615292 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=O)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:22]=[C:21]2[C:17]([CH:18]=[N:19][NH:20]2)=[CH:16][CH:15]=1>>[NH:20]1[C:21]2[C:17](=[CH:16][CH:15]=[C:14]([N:13]=[C:6]3[C:5]4[C:9](=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=4)[NH:8][C:7]3=[O:11])[CH:22]=2)[CH:18]=[N:19]1

Participants

3

Reactant 2

HCID 814231H-Indazol-6-amineHCID 957161H-Indole-2,3-dione, 6-bromo-

Product 1

HCID 135988978HCID 135988978, compoundYield 48.1%

Procedure

The title compound (82 mg, 48%) was synthesized as a orange red solid according to the method described for Example A74 using 6-bromoisatin (113 mg, 0.5 mmol), 6-aminoindazole (73 mg, 0.55 mmol). 1H NMR indicated a 83:17 mixture of E/Z isomers. 1H NMR (400 MHz, DMSO-d6) δ 13.07 (s, 1H, NH), 10.93 (brs, 1H, NH), 8.09 (s, 1H), 7.84 (d, J=8.4 Hz, 1H), 7.08 (s, 1H), 7.05 (d, J=1.6 Hz, 1H), 6.92 (dd, J=8.0 Hz, 1.6 Hz, 1H), 6.77 (dd, J=8.4 Hz, 1.2 Hz, 1H), 6.27 (d, J=8.0 Hz, 1H); MS ESI 341.1 [M+H]+, calcd for [C15H9BrN4O+H]+ 341.1.

Workup

  1. additiona 83:17 mixture of E/Z isomers

Sources & evidence

ORD record
ord-9db4c5681a454d07bc7acf989564ceca
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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