Phosphine → HCID 69883566, compound

HRID 2084061Notes

Reaction equation

HRID 2084061 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].P.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C1(C)C(C)=CC=CC=1.ClCCl.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Pd+2]>[CH:11]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([CH:23]3[CH2:24][NH:25][CH2:26][CH2:27][N:22]3[CH3:21])[CH:10]=2)[CH:6]=[CH:7]1)([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 24404PhosphineHCID 531671-MethylpiperazineHCID 22732008HCID 22732008, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 69883566HCID 69883566, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 5486778Palladium acetylacetonateCatalystHCID 6344DichloromethaneSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-bromo-1-isopropylindole (23.8 mg, 0.1 mmol), sodium-tbutoxide (NaOtBu; 14.1 mg, 0.15 mmol), tri-tbutyl phosphine (tBu3P; 1 mg), palladium acetylacetonate (Pd(OAc)2; 1 mg) and 1-methylpiperazine (60 mg, 0.6 mmol) in xylene (1 ml) under argon was heated at 120° C. for 3 h., The cooled reaction mixture was diluted with dichloromethane, washed with water and the crude product purified by column chromatography on silica gel, eluting with 1% 2M ammonia/methanol in dichloromethane to give (11.3 mg, 44%) of the title compound.

Workup

  1. customThe cooled reaction mixture
  2. washwashed with water
  3. customthe crude product purified by column chromatography on silica gel
  4. washeluting with 1% 2M ammonia/methanol in dichloromethane

Sources & evidence

ORD record
ord-b8fc9cc829764ef38571eda4ceeaaa98
Source dataset
uspto-grants-2004_04
Patent number
US06716837B1

Reaction notes

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