Triethylamine → HCID 86756923, compound

HRID 1979225Notes

Reaction equation

HRID 1979225 reaction equation
[C:1]([O:5][C:6]([CH:8]([C@@H:12]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:13]([NH:15][NH:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:9][CH:10]=[CH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([C@H:8]([C@@H:12]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:13]([NH:15][NH:16][CH2:17][CH:18]([CH3:19])[CH3:20])=[O:14])[CH2:9]/[CH:10]=[CH:11]/[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 122863-BromopyridineHCID 80271Tri-o-tolylphosphineHCID 86756922HCID 86756922, compound

Product 1

HCID 86756923HCID 86756923, compoundYield 14.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 0.500 g of 2(R)-[1(RS)-(tert-butoxycarbonyl)-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in 10 ml of dimethylformamide was treated with 0.465 g of 3-bromopyridine, 0.297 g of triethylamine, 0.017 g of palladium(II) acetate and 0.045 g of tri-(o-tolyl)phosphine. The mixture was heated at 100° C. for 24 hours. After cooling to room temperature the mixture was diluted with water and extracted three times with ethyl acetate. The combined ethyl acetate extracts were washed with water and brine and then dried over anhydrous magnesium sulphate. Evaporation of the solvents and flash column chromatography of the residue on silica gel using ethyl acetate/hexane gave 0.090 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-(3-pyridyl)-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in the form of a yellow oil.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted three times with ethyl acetate
  3. washThe combined ethyl acetate extracts were washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customEvaporation of the solvents and flash column chromatography of the residue on silica gel

Sources & evidence

ORD record
ord-4ca6afe5f9ae4cb7aa030877866e9578
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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