Acetic Anhydride → HCID 66779757, compound

HRID 712571Notes

Reaction equation

HRID 712571 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=3)=[CH:9][N:8]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:5]2=[N:6][CH:7]=1.C(N(CC)CC)C.[C:36](OC(=O)C)(=[O:38])[CH3:37].CCOC(C)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([CH2:15][NH:16][C:36](=[O:38])[CH3:37])=[CH:17][CH:18]=3)=[CH:9][N:8]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:20])=[O:21])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 667783594-[5-bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-benzylamine

Product 1

HCID 66779757HCID 66779757, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[5-Bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-benzylamine (Intermediate CB, 45 mg, 0.1 mmol) was combined with triethylamine (45 μl, 0.3 mmol) and acetic anhydride (11 μl, 0.11 mmol) in anh. DCM (2 ml). The mixture was stirred for 2 hrs, EtOAc, was added and washed with 0.5 N HCl, saturated NaHCO3, water and brine. Evaporation yielded the title compound (48 mg, 96%). MS ESI (m/z): 498.1/500.1 (M+1)+, calc. 497/499.

Workup

  1. washwashed with 0.5 N HCl, saturated NaHCO3, water and brine
  2. customEvaporation

Sources & evidence

ORD record
ord-3b8d39fa73e646d3b5e852cdee7b941f
Source dataset
uspto-grants-2015_11
Patent number
US09181247B2

Reaction notes

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