Triphenylphosphine → HCID 25019578, compound

HRID 2076317Notes

Reaction equation

HRID 2076317 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3I)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 3

HCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 67095932HCID 67095932, compound

Product 1

HCID 25019578HCID 25019578, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

(R)-Indan-1-yl-(5-iodo-quinolin-2-yl)-amine (150 mg, 0.39 mmol) was dissolved in 5 mL 1,2-dimethoxyethane and 2.5 mL 1M sodium carbonate solution. Phenylboronic acid (59 mg, 0.48 mmol) was added. Argon was bubbled through the solution for 2 minutes to remove oxygen. Triphenylphosphine (11 mg, 0.04 mmol) and Palladium acetate (4 mg, 0.02 mmol) were added. The reaction mixture was refluxed overnight. The reaction was diluted with 50 mL water and the mixture was extracted three times with ethyl acetate (100 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->80:20 gradient). The title compound was obtained as a colorless solid (114 mg, 87%), MS: m/e=337.4 (M+H+).

Workup

  1. customArgon was bubbled through the solution for 2 minutes
  2. customto remove oxygen
  3. temperatureThe reaction mixture was refluxed overnight
  4. extractionthe mixture was extracted three times with ethyl acetate (100 mL each)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->80:20 gradient)

Sources & evidence

ORD record
ord-b7a9dfe59b1146e5a3ca757d4b72541f
Source dataset
uspto-grants-2011_04
Patent number
US07923561B2

Reaction notes

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