Methyl 4-(chlorocarbonyl)benzoate → HCID 68252631, compound

HRID 2405093Notes

Reaction equation

HRID 2405093 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH:11][C:12](=[O:18])OC(C)(C)C)=[CH:10][C:5]=2[N:4]([CH3:19])[CH:3]=1.ClC([C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)=O>Cl>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH:11][C:12]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=3)=[O:18])=[CH:10][C:5]=2[N:4]([CH3:19])[CH:3]=1

Participants

4

Reactant 2

HCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 68252634HCID 68252634, compound

Product 1

HCID 68252631HCID 68252631, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In a 125 ml round bottom flask, tert-butyl 3-bromo-1-methyl-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (3G, 0.6 g, 1.839 mmol) was dissolved in 4N HCl (15 ml) and the mixture was stirred at room temperature for 3 h. After completion, volatiles were evaporated and the mixture was re-dissolved in DMA (10 ml). To this was added methyl 4-(chlorocarbonyl)benzoate (0.44 g, 2.2 mmol) and the mixture was stirred at 50° C. for five hours. The reaction was poured into ice water. The precipitated product was collected and dried to obtain the product methyl 4-(3-bromo-1-methyl-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamoyl)benzoate (3H, 0.6 g, 84%). Small amount of debrominated product was observed.

Workup

  1. customAfter completion, volatiles were evaporated
  2. dissolutionthe mixture was re-dissolved in DMA (10 ml)
  3. stirringthe mixture was stirred at 50° C. for five hours
  4. customThe precipitated product was collected
  5. customdried

Sources & evidence

ORD record
ord-ad1bd5e4f1114058bdc0195353c72080
Source dataset
uspto-grants-2014_08
Patent number
US08802695B2

Reaction notes

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