Dichloromethane → HCID 86674847, compound

HRID 2405095Notes

Reaction equation

HRID 2405095 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)[CH3:3].C(Cl)(=O)C(Cl)=O.ClCCl.[Br:22][C:23]1[C:27]2[CH:28]=[N:29][C:30]([NH2:32])=[CH:31][C:26]=2[N:25]([CH3:33])[CH:24]=1>C1(C)C=CC=CC=1>[Br:22][C:23]1[C:27]2[CH:28]=[N:29][C:30]([NH:32][C:8](=[O:10])[C:7]3[CH:6]=[CH:5][C:4]([C:2]([CH3:3])=[CH2:1])=[CH:12][CH:11]=3)=[CH:31][C:26]=2[N:25]([CH3:33])[CH:24]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 2779194-(Prop-1-en-2-yl)benzoic acidHCID 67356473HCID 67356473, compound

Product 1

HCID 86674847HCID 86674847, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 50 ml round bottom flask, 4-(prop-1-en-2-yl)benzoic acid (580 mg, 3.6 mmol) was dissolved in 15 ml toluene, and 2.0 M oxalyl chloride in dichloromethane (3.6 ml, 7.2 mmol) was added slowly. Stirring continued for 3 hours, and then volatiles were evaporated from the reaction mixture. To the residue was added 5 ml toluene and the mixture was concentrated in vacuo to azeotropically remove residual water. The residue was then dissolved in DMA (12 ml) and 3-bromo-1-methyl-1H-pyrrolo[3,2-c]pyridin-6-amine (400 mg, 1.8 mmol) was added. Stirring continued at 50° C. for another 3 hours. The mixture was then poured into ice water. The precipitate was collected and dried to obtain the product N-(3-bromo-1-methyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-4-(prop-1-en-2-yl)benzamide (6A, 440 mg, 67%). This was used in the next step without further purification.

Workup

  1. customvolatiles were evaporated from the reaction mixture
  2. additionTo the residue was added 5 ml toluene
  3. concentrationthe mixture was concentrated in vacuo to azeotropically remove residual water
  4. dissolutionThe residue was then dissolved in DMA (12 ml)
  5. stirringStirring
  6. waitcontinued at 50° C. for another 3 hours
  7. customThe precipitate was collected
  8. customdried

Sources & evidence

ORD record
ord-372a762e4786438cb09ec74159445349
Source dataset
uspto-grants-2014_08
Patent number
US08802695B2

Reaction notes

Loading…