Methanol → 1H-Pyrrolo[2,3-B]pyridine-5-carboxylic acid, 1-[(4-methylphenyl)sulfonyl]-, methyl ester

HRID 269486Notes

Reaction equation

HRID 269486 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.CCN(CC)CC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:47][OH:48].CN([CH:52]=[O:53])C>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:47][O:48][C:52]([C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1)=[O:53]

Participants

7

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 224773531H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(4-methylphenyl)sulfonyl]-

Product 1

HCID 497589101H-Pyrrolo[2,3-B]pyridine-5-carboxylic acid, 1-[(4-methylphenyl)sulfonyl]-, methyl ester

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Under N2 purge, 5-Bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.0 g, 2.8 mmol), Et3N (0.75 mL, 5.4 mmol), Pd(OAc)2 (64 mg, 0.28 mmol), Ph3P (0.45 g, 1.7 mmol) and MeOH (5.0 mL, 120 mmol) were loaded in 20 mL DMF. The vessel was purged with CO 5 minutes and fixed with a condenser tube with CO balloon. The reaction was heated to 100 C for 6 hours and monitored by TLC (rf 5-Bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine=0.72, rf 1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester=0.43, CH2Cl2). After 6 hours, the reaction was removed from heat, diluted to 100 mL with water and extracted with EtOAC (100 mL). The phases were separated and organic was washed with additional water (2×100 mL) and brine (1×100 mL), dried over Na2SO4, filtered, and dried in vacuo. The resulting yellow powder was purified over a short plug of silica gel with CH2Cl2 until all material was recovered. Yield 0.94 g, white powder.

Workup

  1. customUnder N2 purge
  2. customThe vessel was purged with CO 5 minutes
  3. customfixed with a condenser tube with CO balloon
  4. temperatureThe reaction was heated to 100 C for 6 hours
  5. customthe reaction was removed
  6. temperaturefrom heat
  7. additiondiluted to 100 mL with water
  8. extractionextracted with EtOAC (100 mL)
  9. customThe phases were separated
  10. washorganic was washed with additional water (2×100 mL) and brine (1×100 mL)
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. customdried in vacuo
  14. customThe resulting yellow powder was purified over a short plug of silica gel with CH2Cl2 until all material
  15. customwas recovered

Sources & evidence

ORD record
ord-1987b6f7d1a94322b325468df9f70235
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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