Triethylamine → HCID 69588931, compound

HRID 2181150Notes

Reaction equation

HRID 2181150 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8]([O:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]=[CH2:21])=[O:14])([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(#N)C>[C:8]([O:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1/[CH:20]=[CH:21]/[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 122863-BromopyridineHCID 516892Sodium BicarbonateHCID 11084803(2S)-N-tert-butoxycarbonyl-2-vinylpyrrolidine

Product 1

HCID 69588931HCID 69588931, compoundYield 119.9%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

In a sealed pressure tube under a nitrogen atmosphere, 3-bromopyridine (264.67 mg, 1.675 mmol), (2S)-N-tert-butoxycarbonyl-2-vinylpyrrolidine (300 mg, 1.52 mmol), tri-o-tolylphosphine (46.82 mg, 0.153 mmol), palladium(II) acetate (34.53 mg, 0.15 mmol), triethylamine (2 mL) and acetonitrile (20 mL) were stirred at 90° C. for 14 h. The tube was cooled and the contents were slowly poured into a stirred saturated aqueous NaHCO3 solution (20 mL) and extracted with chloroform (4×20 mL). The combined chloroform extracts were dried (K2CO3), filtered and concentrated under vacuum to give 500 mg of a viscous dark oil, which was chromatographed with an ethyl acetate:hexane gradient (1:4 to 1:1, v/v) as eluant. Selected fractions containing the product were combined and concentrated on a rotary evaporator to give 310 mg (84.0% yield) of pale-yellow oil.

Workup

  1. temperatureThe tube was cooled
  2. extractionextracted with chloroform (4×20 mL)
  3. dry with materialThe combined chloroform extracts were dried (K2CO3)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cd2a5316554643cfa376ff0f0d2ded05
Source dataset
uspto-grants-2005_05
Patent number
US06890935B2

Reaction notes

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