Hydrochloric Acid → HCID 54024436, compound

HRID 1432894Notes

Reaction equation

HRID 1432894 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1.C(N(CCCC)CCCC)CCC.[C:25]([OH:29])(=[O:28])[CH:26]=[CH2:27].Cl>O.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:9]([NH:8][C:5]1[N:6]=[CH:7][C:2]([CH:27]=[CH:26][C:25]([OH:29])=[O:28])=[CH:3][CH:4]=1)(=[O:11])[CH3:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6581Acrylic AcidHCID 7622TributylamineHCID 2930972-Acetamido-5-bromopyridine

Product 1

HCID 54024436HCID 54024436, compoundYield 66.2%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

To a mixture of N-(5-bromo-pyridin-2-yl)-acetamide (1.26 g, 5.86 mmol) and tri-n-butylamine in xylenes (10 mL) is added Pd(OAc)2 (1.4 mg, 0.006 mmol) and triphenyl phosphine (15.4 mg, 0.06 mmol). Acrylic acid (0.48 mL, 7.03 mmol) is then added dropwise over 5 minutes. The mixture is heated to reflux for 5 hours. The solution is cooled to ambient temperatures. The mixture is diluted with water and the pH is adjusted to 4 with 1N HCl. The solution is extracted with EtOAc/CH2Cl2 (2:1). The resulting suspension is filtred to give the title compound (0.80 g, 3.88 mmol) as a white solid. MS (ion spray) 207, (M+H).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 5 hours
  3. temperatureThe solution is cooled to ambient temperatures
  4. extractionThe solution is extracted with EtOAc/CH2Cl2 (2:1)

Sources & evidence

ORD record
ord-1a0c07ab79f34b3d971b755b9288bfd3
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

Loading…