Acetic Acid → [2-(4-Chloro-phenyl)-5,6-difluoro-2H-indazol-3-yl]-cyclohexyl-amine

HRID 1690539Notes

Reaction equation

HRID 1690539 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([NH2:17])=[C:15]3[C:10]([CH:11]=[C:12]([F:19])[C:13]([F:18])=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[C:20]1(=O)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]([NH:17][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[C:15]3[C:10]([CH:11]=[C:12]([F:19])[C:13]([F:18])=[CH:14]3)=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 5049666Sodium triacetoxyborohydrideHCID 669051692-(4-Chloro-phenyl)-5,6-difluoro-2H-indazol-3-ylamine

Product 1

HCID 66905283[2-(4-Chloro-phenyl)-5,6-difluoro-2H-indazol-3-yl]-cyclohexyl-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to the procedure described in example 1.1, a mixture of 2-(4-chloro-phenyl)-5,6-difluoro-2H-indazol-3-ylamine and cyclohexanone ([108-94-1]) was reacted with sodium triacetoxyborohydride in the presence of acetic acid in CH2Cl2 under reflux conditions for 96 h to give the title compound as light brown solid. MS: m/e=362.5 [M+H+].

Sources & evidence

ORD record
ord-21bc9d34f77f4cc087271ff3f9a10570
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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