Potassium vinyltrifluoroborate → HCID 66896108, compound

HRID 2045729Notes

Reaction equation

HRID 2045729 reaction equation
[B-](F)(F)(F)[CH:2]=[CH2:3].[K+].Cl[C:9]1[C:10]([O:19][C@H:20]2[CH2:24][N:23]([C:25](=[O:46])[C@H:26]([CH:41]3[CH2:45][CH2:44][CH2:43][CH2:42]3)[NH:27][C:28]([N:30]3[CH2:34][CH2:33][C@H:32]([O:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH2:40])[CH2:31]3)=[O:29])[C@H:22]([C:47]([O:49][CH3:50])=[O:48])[CH2:21]2)=[N:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2>CCO.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:41]1([C@H:26]([NH:27][C:28]([N:30]2[CH2:34][CH2:33][C@H:32]([O:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH2:40])[CH2:31]2)=[O:29])[C:25]([N:23]2[CH2:24][C@H:20]([O:19][C:10]3[C:9]([CH:2]=[CH2:3])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:11]=3)[CH2:21][C@H:22]2[C:47]([O:49][CH3:50])=[O:48])=[O:46])[CH2:45][CH2:44][CH2:43][CH2:42]1

Participants

5

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 87195837HCID 87195837, compound

Product 1

HCID 66896108HCID 66896108, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 702EthanolSolvent

Procedure

Potassium trifluoro(vinyl)borate (68 mg, 0.513 mmol), TEA (0.071 mL, 0.513 mmol) and PdCl2(dppf)-CH2Cl2 adduct (28 mg, 0.034 mmol) were added in sequence to a solution of methyl (4R)-4-[(3-chloroquinoxalin-2-yl)oxy]-1-[(25)-2-cyclopentyl-2-({[(35)-3-(pent-4-en-1-yloxy)pyrrolidin-1-yl]carbonyl}amino)acetyl]-L-prolinate (210 mg, 0.342 mmol) in EtOH (4 mL). The resulting mixture was refluxed for 1 h, then concentrated under reduced pressure to give a residue that was purified on silica gel (gradient elution from 10% to 50% AcOEt in petroleum ether) to afford the title compound (163 mg, 79%) as a solid. LCMS (ES+) m/z 606 (M+H)+.

Workup

  1. temperatureThe resulting mixture was refluxed for 1 h
  2. concentrationconcentrated under reduced pressure
  3. customto give a residue that
  4. customwas purified on silica gel (gradient elution from 10% to 50% AcOEt in petroleum ether)

Sources & evidence

ORD record
ord-c9a252bbb0de4e1ba5e9563a6157a61d
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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