Ammonium Chloride → 1-Benzyl-3-(2-pyrimidyl)indazole

HRID 1935645Notes

Reaction equation

HRID 1935645 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([Sn](C)(C)C)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:22]1[N:27]=[CH:26][CH:25]=[CH:24][N:23]=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1.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>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 744042-ChloropyrimidineHCID 158403561-Benzyl-3-trimethylstannylindazole

Product 1

HCID 184166611-Benzyl-3-(2-pyrimidyl)indazole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

200 mg of 1-benzyl-3-trimethylstannylindazole (crude product, 70% according to GC), 35 mg of 2-chloropyrimidine (0.30 mmol) and 29 mg (0.025 mmol) of Pd(PPh3)4 in 2.5 ml of toluene were heated under reflux overnight in an argon atmosphere. The mixture was cooled to room temperature, saturated ammonium chloride solution was added and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulphate and freed from the solvent on a rotary evaporator. Purification was carried out by chromatography over aluminium oxide using cyclohexane/ethyl acetate as the eluent (gradient from 10:1 to 1:1).

Workup

  1. temperatureunder reflux overnight in an argon atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customfreed from the solvent on a rotary evaporator
  5. customPurification

Sources & evidence

ORD record
ord-b2b5a06c2b5f4118aa99a462ed8e4085
Source dataset
uspto-grants-2002_05
Patent number
US06387940B1

Reaction notes

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