Methanol → HCID 58306783, compound

HRID 1909877Notes

Reaction equation

HRID 1909877 reaction equation
Br[C:2]1[C:3]2[N:10](C(OC(C)(C)C)=O)[CH:9]=[CH:8][C:4]=2[CH:5]=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN([CH:50]=[O:51])C.[CH3:52][OH:53]>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[NH:10]1[C:3]2[C:2]([C:52]([O:51][CH3:50])=[O:53])=[CH:7][N:6]=[CH:5][C:4]=2[CH:8]=[CH:9]1

Participants

8

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 58306925HCID 58306925, compound

Product 1

HCID 58306783HCID 58306783, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl 7-bromo-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (0.20 g), 1,3-bis(diphenylphosphino)propane (0.028 g), palladium acetate (0.015 g), DMF (4.0 mL), methanol (6.0 mL), and triethylamine (0.28 mL) was stirred at 80° C. for 2 days under carbon monoxide atmosphere. The reaction mixture was left to be cooled and replaced with argon. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then filtered. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=30 to 60%) to obtain methyl 1H-pyrrolo[3,2-c]pyridine-7-carboxylate (0.081 g).

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=30 to 60%)

Sources & evidence

ORD record
ord-513c7a5292bc48439693129aefc1bbde
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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