Triphenylphosphine → HCID 58515063, compound

HRID 1948722Notes

Reaction equation

HRID 1948722 reaction equation
Cl[C:2]1[C:11]([CH2:12][OH:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:41]1([CH3:50])[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1B(O)O>O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:50][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[C:2]1[C:11]([CH2:12][OH:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 930708(2-chloroquinolin-3-yl)methanolHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 58515063HCID 58515063, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (2-chloro-3-quinolinyl)methanol (500 mg, 2.60 mmol), potassium phosphate tribasic (770 mg, 3.60 mmol), Pd(OAc)2 (30 mg, 0.13 mmol), PPh3 (136 mg, 0.52 mmol) and o-tolylboronic acid (530 mg, 3.90 mmol) in water (4.0 mL) was degassed. DME (13 mL) was added and the mixture was degassed further, then heated at 120° C. for 30 minutes. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 10% aqueous potassium carbonate solution. The aqueous phase was extracted with further EtOAc and the combined organic fractions were dried (MgSO4) and evaporated in vacuo. The residue was purified by column chromatography (SiO2, 10-40% EtOAc in heptane) then by preparative HPLC (Method 2). The product obtained was partitioned between DCM and 10% aqueous K2CO3 solution. The organic phase was dried (MgSO4) and evaporated in vacuo to give the title compound (240 mg, 37%) as a clear gum. δH (CDCl3) 8.34 (s, 1H), 8.12-8.17 (m, 1H), 7.86-7.91 (m, 1H), 7.69-7.76 (m, 1H), 7.54-7.62 (m, 1H), 7.18-7.37 (m, 4H), 4.52 (br. d, J 4.3 Hz, 2H), 2.40 (br. t, J 5.1 Hz, 1H), 2.07 (s, 3H). LCMS (ES+) 250.1 (M+H)+, RT 3.17 minutes (Method 4).

Workup

  1. customwas degassed
  2. additionDME (13 mL) was added
  3. customthe mixture was degassed further
  4. customThe solvent was removed in vacuo
  5. customthe residue was partitioned between EtOAc and 10% aqueous potassium carbonate solution
  6. extractionThe aqueous phase was extracted with further EtOAc
  7. dry with materialthe combined organic fractions were dried (MgSO4)
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography (SiO2, 10-40% EtOAc in heptane)
  10. customThe product obtained
  11. customwas partitioned between DCM and 10% aqueous K2CO3 solution
  12. dry with materialThe organic phase was dried (MgSO4)
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-375895b7c5494b7dae5e109c267a70a3
Source dataset
uspto-grants-2013_03
Patent number
US08399483B2

Reaction notes

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