Water → 6-amino-5-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile

HRID 595701Notes

Reaction equation

HRID 595701 reaction equation
[Br:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][C:8]2[C:4](=[C:5]([C:21]#[N:22])[N:6]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[N:7]=2)[CH:3]=1.C1COCC1.O.[Cl-].[NH4+]>CO.[Fe]>[NH2:11][C:10]1[C:2]([Br:1])=[CH:3][C:4]2[C:8]([CH:9]=1)=[N:7][N:6]([C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)[C:5]=2[C:21]#[N:22]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 677773475-bromo-2-(4-fluorophenyl)-6-nitro-2H-indazole-3-carbonitrile

Product 1

HCID 903324396-amino-5-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrileYield 68%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 5-bromo-2-(4-fluorophenyl)-6-nitro-2H-indazole-3-carbonitrile (500 mg, 139 mmol) in a mixture of methanol (50 mL), THF (5 mL) and water (2.5 mL) was added ammonium chloride (370 mg, 6.91 mmol) followed by iron powder (386 mg, 6.91 mmol). The mixture was heated to 80° C. and stirred vigorously for 90 min. The resulting suspension was filtered through celite and washed with EtOAc. The filtrate was concentrated, and the residue was suspended in water and extracted with EtOAc. The organic layer was contracted to give 6-amino-5-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile (310 mg, 68%) as a yellow solid. 1H-NMR (CDCl3, 400 MHz) δ 7.99 (s, 1H), 7.80˜7.82 (m, 2H), 7.23˜7.57 (m, 2H), 7.03 (s, 1H), 4.40 (s, 2H). MS (M+H)+: 331/333.

Workup

  1. filtrationThe resulting suspension was filtered through celite
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-55771fbc1eb346fb89c915faa9bb3afe
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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