Triphenylphosphine → HCID 68334860, compound

HRID 2371027Notes

Reaction equation

HRID 2371027 reaction equation
Br[C:2]1[S:10][C:9]2[CH2:8][CH2:7][O:6][CH:5]([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:4]=2[CH:3]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22](B(O)O)[CH:21]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:2]2[S:10][C:9]3[CH2:8][CH2:7][O:6][CH:5]([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:4]=3[CH:3]=2)[CH:21]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 27343783-Pyridinylboronic acidHCID 68335097HCID 68335097, compound

Product 1

HCID 68334860HCID 68334860, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl (2-bromo-6,7-dihydro-4H-thieno[3,2-c]pyran-4-yl)methylcarbamate (500 mg, 1.44 mmol), pyridine-3-boronic acid (351 mg, 2.88 mmol), Pd(OAc)2 (33 mg), PPh3 (170 mg, 0.65 mmol) in 1,4-dioxane was purged with nitrogen. After stirring at room temperature for 0.5 hr, 457 mg of Na2CO3 in 3 mL of H2O was added. The reaction mixture was stirred at 100° C. for 2 hr. After cooling to room temperature, the reaction mixture was poured into 100 mL of water and extracted with EtOAc twice. The combined organic layers were washed with brine, dried over Na2SO4, concentrated and purified by column chromatography to give the desired product.

Workup

  1. customwas purged with nitrogen
  2. addition457 mg of Na2CO3 in 3 mL of H2O was added
  3. stirringThe reaction mixture was stirred at 100° C. for 2 hr
  4. temperatureAfter cooling to room temperature
  5. additionthe reaction mixture was poured into 100 mL of water
  6. extractionextracted with EtOAc twice
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-e60f8c6d65ea4c7996bc93c0ab6bc67b
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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