Triphenyl phosphite → HCID 59642997, compound

HRID 2251604Notes

Reaction equation

HRID 2251604 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:23]([O:25][CH3:26])=[O:24])[C:5]2[O:9][C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:7][C:6]=2[CH:22]=1.[CH3:27][N:28]([CH3:33])[C:29](=[O:32])[CH:30]=[CH2:31].P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CC(N(C)C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:27][N:28]([CH3:33])[C:29](/[CH:30]=[CH:31]/[C:2]1[CH:3]=[C:4]([C:23]([O:25][CH3:26])=[O:24])[C:5]2[O:9][C:8]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:7][C:6]=2[CH:22]=1)=[O:32]

Participants

8

Reactant 4

HCID 7540Triphenyl phosphiteHCID 10340Sodium CarbonateHCID 17587N,N-DimethylacrylamideHCID 59642990Methyl 6-bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylate

Product 1

HCID 59642997HCID 59642997, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Procedure

A solution of methyl 6-bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylate (130 mg, 0.32 mmol), N,N-dimethylacrylamide (47 mg, 0.47 mmol, 1.5 eq.), P(OPh)3 (980 mg, 3.16 mmol, 10 eq.), Bu4NBr (20 mg, 0.06 mmol, 0.2 eq.), Na2CO3 (40 mg, 0.38 mmol, 1.2 eq.) and Pd(OAc)2 (10 mg, 0.03 mmol, 0.1 eq.) in 10 mL dimethylacetamide was stirred at 140° C. for 72 h. After cooling to r.t. the mixture was partitioned between EtOAc and H2O. The organic layer was washed twice with saturated NaCl solution, dried over MgSO4 and evaporated in vacuo. The crude product was purified using flash chromatography (silica gel, hexane/EtOAc 5:1→3:2) to yield the desired compound as a colorless, slowly solidifying viscous oil.

Workup

  1. customwas partitioned between EtOAc and H2O
  2. washThe organic layer was washed twice with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-99364209eda84cbdbdac7ec7e2bf2e4e
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

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