Dimethylformamide → HCID 178426383, compound

HRID 1610130Notes

Reaction equation

HRID 1610130 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
  7. wash(ethyl acetate:n-hexane=1:10 to 1:1) and the resulting crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-9682b7035f46473aabf032c85ecb0fc1
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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