Potassium vinyltrifluoroborate → HCID 66962889, compound

HRID 2060370Notes

Reaction equation

HRID 2060370 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[O:12][C@H:13]2[CH2:17][N:16]([C:18](=[O:36])[C@H:19]([CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[NH:20][C:21]([O:23][CH2:24][C:25]([CH3:30])([CH3:29])[CH2:26][CH:27]=[CH2:28])=[O:22])[C@H:15]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:14]2)=[CH:4][CH:3]=1.[CH:42]([B-](F)(F)F)=[CH2:43].[K+]>C(O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH:31]1([C@H:19]([NH:20][C:21]([O:23][CH2:24][C:25]([CH3:29])([CH3:30])[CH2:26][CH:27]=[CH2:28])=[O:22])[C:18]([N:16]2[CH2:17][C@H:13]([O:12][C:9]3[C:10]4[C:5](=[CH:4][CH:3]=[C:2]([CH:42]=[CH2:43])[CH:11]=4)[CH:6]=[CH:7][N:8]=3)[CH2:14][C@H:15]2[C:37]([O:39][CH2:40][CH3:41])=[O:38])=[O:36])[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

5

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 66963177HCID 66963177, compound

Product 1

HCID 66962889HCID 66962889, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 702EthanolSolvent

Procedure

Ethyl(4R)-4-[(7-bromoisoquinolin-1-yl)oxy]-1-[(2S)-2-cyclopentyl-2-({[(2,2-dimethylpent-4-en-1-yl)oxy]carbonyl}amino)acetyl]-L-prolinate (526 mg, 0.83 mmol) was dissolved in ethanol (10 mL) and nitrogen was bubbled through for 15 min. Potassium vinyltrifluoroborate (168 mg, 1.25 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) DCM adduct (34 mg, 0.04 mmol) were added and the reaction mixture heated to reflux under nitrogen. After 15 h, the reaction was complete and the volatiles were evaporated and the residue purified by silica gel chromatography (gradient elution, 10-75% EtOAc/hexane) to give a clear oil. LRMS (ESI) m/z 578.4 [(M+H)+; calcd for C33H44N3O6: 578.3].

Workup

  1. customnitrogen was bubbled through for 15 min
  2. temperaturethe reaction mixture heated
  3. temperatureto reflux under nitrogen
  4. customthe volatiles were evaporated
  5. customthe residue purified by silica gel chromatography (gradient elution, 10-75% EtOAc/hexane)
  6. customto give a clear oil

Sources & evidence

ORD record
ord-ee27d449c84a45d3b90936d267e6f1a0
Source dataset
uspto-grants-2012_10
Patent number
US08278322B2

Reaction notes

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