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

HRID 1037533Notes

Reaction equation

HRID 1037533 reaction equation
[NH2:1][C:2]1[C:3]([CH:22]2[CH2:24][CH2:23]2)=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)[C:6]=2[C:18]([NH:20][CH3:21])=[O:19].[CH:25](=O)[CH3:26].C([BH3-])#N.[Na+]>CO>[Br:17][C:14]1[CH:13]=[CH:12][C:11]([N:7]2[C:6]([C:18]([NH:20][CH3:21])=[O:19])=[C:5]3[C:9]([CH:10]=[C:2]([NH:1][CH2:25][CH3:26])[C:3]([CH:22]4[CH2:24][CH2:23]4)=[CH:4]3)=[N:8]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 675127246-amino-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide

Product 1

HCID 675178472-(4-bromophenyl)-5-cyclopropyl-6-(ethylamino)-N-methyl-2H-indazole-3-carboxamideYield 32.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 6-amino-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide (i) (20 mg, 0.052 mmol) in MeOH (0.6 mL) was added acetaldehyde (15 μL 0.27 mmol) at 0° C. Sodium cyanoborohydride (5 mg, 0.078 mmol) was then added and the mixture was stirred at RT for 1 h. The mixture was filtered and the filtrate was concentrated to dryness. The residue was purified by reverse phase flash column chromatography eluting with ACN/water (5-100%) to give 2-(4-bromophenyl)-5-cyclopropyl-6-(ethylamino)-N-methyl-2H-indazole-3-carboxamide (ii) as a white solid (7 mg, 32%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was purified by reverse phase flash column chromatography
  4. washeluting with ACN/water (5-100%)

Sources & evidence

ORD record
ord-511d55668239446e99e7bd3a14895963
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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