Dimethylformamide → HCID 86659712, compound

HRID 2401016Notes

Reaction equation

HRID 2401016 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=[O:12])[CH:9]=2)[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[C:21]([F:24])([F:23])[F:22])[N:3]=1.C([O-])(=O)C.[Na+].[CH3:30][N:31](C=O)C>[C-]#N.[Zn+2].[C-]#N>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:4]2[C:5]3[C:10](=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][CH:6]=3)[C:2]([C:30]#[N:31])=[N:3]2)=[C:15]([C:21]([F:24])([F:23])[F:22])[CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 866597093-Bromo-1-(4-chloro-2-trifluoromethylbenzyl)-1H-indazole-5-carbaldehyde

Product 1

HCID 86659712HCID 86659712, compound

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-1-(4-chloro-2-trifluoromethylbenzyl)-1H-indazole-5-carbaldehyde (0.479 mmol, from Example 407), Pd(dppf)Cl2 dichloromethane complex (0.0479 mmol), zinc cyanide (0.575 mmol), and sodium acetate (0.958 mmol) in DMF (6 mL) under argon was heated at 100° C. for 4 h, then concentrated under reduced pressure. Chromatographic purification of the residue (silica gel, hexanes to hexanes:EtOAc, 1:1) afforded 1-(4-Chloro-2-trifluoromethylbenzyl)-5-formyl-1H-indazole-3-carbonitrile as yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customChromatographic purification of the residue (silica gel, hexanes to hexanes:EtOAc, 1:1)

Sources & evidence

ORD record
ord-2fbf3388a37e4d738364769bb7bd4edb
Source dataset
uspto-grants-2014_08
Patent number
US08796256B2

Reaction notes

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