Water → 4-(4-bromo-2-methoxyphenyl)-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 930898Notes

Reaction equation

HRID 930898 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:18]=[CH:17][N:16](S(C4C=CC(C)=CC=4)(=O)=O)[C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)=[C:4]([O:29][CH3:30])[CH:3]=1.[OH-].[K+].O>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:18]=[CH:17][NH:16][C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)=[C:4]([O:29][CH3:30])[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 867210614-(4-bromo-2-methoxyphenyl)-6-methyl-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

Product 1

HCID 867210634-(4-bromo-2-methoxyphenyl)-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-oneYield 73.2%

Reagents, catalysts & solvents 2

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 312751,4-DioxaneSolvent

Procedure

The product from Example 241a (0.2 g, 0.410 mmol), potassium hydroxide (0.460 g, 8.21 mmol) and cetyltrimethylammonium bromide (7.48 mg, 0.021 mmol) were combined in dioxane (8 mL) and water (4 mL) and heated at 100° C. for 18 hours. The reaction mixture was partitioned between equal volumes of ethyl acetate and water and the pH was adjusted to pH 7 by careful addition of concentrated HCl. The organic layer was separated and washed three times with saturated aqueous sodium chloride, dried (Na2SO4), filtered, and concentrated. Purification by trituration in dichloromethane afforded the title compound (0.1 g, 73%). 1H NMR (300 MHz, DMSO-d6) δ ppm 11.97 (s, 1H) 7.05-7.42 (m, 5H) 5.87-6.09 (m, 1H) 3.75 (s, 3H) 3.54 (s, 3H). MS (ESI+) m/z 333/335 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between equal volumes of ethyl acetate and water
  2. additionthe pH was adjusted to pH 7 by careful addition of concentrated HCl
  3. customThe organic layer was separated
  4. washwashed three times with saturated aqueous sodium chloride
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by trituration in dichloromethane

Sources & evidence

ORD record
ord-327506b391d94f9681ca7073f937c5b3
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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