Methanol → 6-amino-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide

HRID 1037526Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:19][CH3:20])=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([N+:24]([O-])=O)[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[Cl-].[NH4+].CO>C(O)C.O.C(Cl)Cl.[Fe]>[NH2:24][C:12]1[C:13]([CH:21]2[CH2:23][CH2:22]2)=[CH:14][C:15]2[C:10]([CH:11]=1)=[N:9][N:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:16]=2[C:17]([NH:19][CH3:20])=[O:18]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of compound (viii) (500 mg, 1.20 mmol) in a mixture of ethanol (30 mL) and water (6 mL) was added ammonium chloride (450 mg, 8.43 mmol) followed by iron powder (470 mg, 8.43 mmol). The mixture was heated to 80° C. and stirred vigorously for 90 min. After cooling to RT, 5% MeOH in DCM solution (50 mL) was added to the reaction mixture. The resulting suspension was filtered through celite and washed with MeOH. The filtrate was concentrated in vacuo to give a yellow solid which was then suspended in water (40 mL) and filtered. The solid was collected and dried to give 6-amino-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide (ix) (320 mg, 68%) as a yellow solid. ESI-MS m/z calculated for [M+H]+: 385.07/387.06; found: 385.12/387.10.

Workup

temperatureAfter cooling to RT
filtrationThe resulting suspension was filtered through celite
washwashed with MeOH
concentrationThe filtrate was concentrated in vacuo
customto give a yellow solid which
filtrationfiltered
customThe solid was collected
customdried

Sources & evidence

ORD record: ord-ea654436141d4bbb9aa3ffd62288db25
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546389B2

Reaction notes

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