Ethyl Acrylate → HCID 66629898, compound

HRID 1411397Notes

Reaction equation

HRID 1411397 reaction equation
Br[C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:7]([C@@H:9]3[CH2:13][CH2:12][CH2:11][N:10]3[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[N:8][C:4]=2[CH:3]=1.[C:31]([O:35][CH2:36][CH3:37])(=[O:34])[CH:32]=[CH2:33].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.C1(CNCC2CCCCC2)CCCCC1>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:36]([O:35][C:31](=[O:34])/[CH:32]=[CH:33]/[C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:26])([CH3:28])[CH3:27])[C:7]([C@@H:9]3[CH2:13][CH2:12][CH2:11][N:10]3[C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])=[N:8][C:4]=2[CH:3]=1)[CH3:37]

Participants

7

Reactant 4

HCID 8821Ethyl AcrylateHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 4594378Bis(cyclohexylmethyl)amineHCID 58226548HCID 58226548, compound

Product 1

HCID 66629898HCID 66629898, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To (S)-tert-butyl 2-(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)pyrrolidine-1-carboxylate (2.973 g, 5.99 mmol), ethyl acrylate (0.714 mL, 6.59 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.104 g, 0.359 mmol), N,N-dicyclohexylmethylamine (1.461 mL, 6.89 mmol), and tris(dibenzylideneacetone)dipalladium(0) (0.164 g, 0.18 mmol) dissolved in THF (18 mL) had nitrogen bubbled through the solution for 15 minutes to remove the oxygen, and then the mixture heated at 60° C. for 2 hours. After cooling to room temperature the solution was filtered through diatomaceous earth and washed with EtOAc. The filtrated was then concentrated to a residue, and then the residue was dissolved in dichloromethane and extracted with water. The organic layer was then dried and concentrated. The residue was purified by chromatography (silica gel, hexanes in ethyl acetate) which afforded 2.56 g, (83%) of the title compound. MS (ESI) m/z 516 (M+H)+.

Workup

  1. custombubbled through the solution for 15 minutes
  2. customto remove the oxygen
  3. temperatureAfter cooling to room temperature the solution
  4. filtrationwas filtered through diatomaceous earth
  5. washwashed with EtOAc
  6. concentrationThe filtrated was then concentrated to a residue
  7. dissolutionthe residue was dissolved in dichloromethane
  8. extractionextracted with water
  9. customThe organic layer was then dried
  10. concentrationconcentrated
  11. customThe residue was purified by chromatography (silica gel, hexanes in ethyl acetate) which

Sources & evidence

ORD record
ord-cb5877b5ecdc47dc90491d01b107bfd1
Source dataset
uspto-grants-2014_12
Patent number
US08921514B2

Reaction notes

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