Dimethylformamide → HCID 178426383, compound

HRID 503174Notes

Reaction equation

HRID 503174 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7](C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[N:6]=[C:5]2[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1.C[N:39]([CH3:42])C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:37][C:33]1[CH:32]=[C:31]([C:5]2[C:4]3[C:8](=[C:9]([CH3:11])[CH:10]=[C:2]([C:42]#[N:39])[CH:3]=3)[NH:7][N:6]=2)[CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 222607405-Bromo-3-(3-fluorophenyl)-7-methyl-1-trityl-1H-indazole

Product 1

HCID 178426383HCID 178426383, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1.5 g of 5-bromo-3-(3-fluorophenyl)-7-methyl-1-trityl-1H-indazole in 15 ml dimethylformamide were added 0.64 g of zinc cyanide and 0.32 g of tetrakis(triphenylphosphine)palladium(0) at room temperature, and the mixture was stirred at 100° C. for one day. At the same temperature, 0.32 g of tetrakis(triphenylphosphine)palladium(0) was added and the mixture was stirred at 130° C. for one day. The reaction mixture was diluted with ethyl acetate, and the organic layer was sequentially washed with saturated aqueous ammonium chloride solution and brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10 to 1:1) and the resulting crystals were washed with diethyl ether, to give 431 mg of the title compound as colorless crystals.

Workup

  1. stirringthe mixture was stirred at 130° C. for one day
  2. washthe organic layer was sequentially washed with saturated aqueous ammonium chloride solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe crude product was purified
  6. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10 to 1:1)
  7. washthe resulting crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-dc478f20e3474db4a9c60e58c35c98b4
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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