Tributylamine → HCID 178516959, compound

HRID 877047Notes

Reaction equation

HRID 877047 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([NH2:11])=[N:7][NH:8]2)=[CH:4][CH:3]=1.[C:12]1([CH:18]([C:24](OCC)=[O:25])[C:19](OCC)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CCCC)CCCC)CCC.[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]1[C:19]([OH:20])=[C:18]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:24]([OH:25])=[N:11][C:6]=21

Participants

6

Reactant 4

HCID 7622TributylamineHCID 14798Sodium HydroxideHCID 66514Diethyl phenylmalonateHCID 27866316-bromo-1H-indazol-3-amine

Product 1

HCID 178516959HCID 178516959, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.9 g (46.7 mmol) 6-Bromo-1H-indazol-3-ylamine, 11 g (46.7 mmol) diethyl phenylmalonate and 19.8 mL (83.1 mmol) tributyl amine were heated for 15 h at 180° C. The reaction mixture was treated with 2M sodium hydroxide and water and extracted three times with tert-butyl methyl ether. The organic phase was discarded and the aqueous phase was acidified with conc. hydrochloric acid. The precipitate was collected by filtration and washed with water to obtain the desired product (16.2 g) which was however contaminated and which was used in the next step without further purification.

Workup

  1. extractionextracted three times with tert-butyl methyl ether
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-e2ccdc84123245c1bc45a47123014ca7
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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