Tetramethyltin → 1-(4-Fluoro-phenyl)-4-hydroxy-7-methyl-3-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642239Notes

Reaction equation

HRID 642239 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][N:13]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:9]2=[C:10](Cl)[N:11]=1)=[O:5])[CH3:2].[CH3:30][Sn](C)(C)C>CN(C=O)C.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][N:13]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:9]2=[C:10]([CH3:30])[N:11]=1)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 11661TetramethyltinHCID 866173507-Chloro-1-(4-fluoro-phenyl)-4-hydroxy-3-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 684263881-(4-Fluoro-phenyl)-4-hydroxy-7-methyl-3-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl esterYield 52.6%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 7-chloro-1-(4-fluoro-phenyl)-4-hydroxy-3-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (60 mg, 0.146 mmol), tetramethyltin (104 mg, 0.584 mmol) and Pd(PPh3)2Cl2 in DMF (1 mL) was stirred at 135° C. for 2 h; then the reaction was cooled, diluted with EtOAc, washed with water and saturated sodium chloride aqueous solution respectively, the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, the residue was purified on column to give the desired title product (30 mg); ESI MS (m/z): 391 (M+H+).

Workup

  1. temperaturethen the reaction was cooled
  2. washwashed with water and saturated sodium chloride aqueous solution respectively
  3. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified on column

Sources & evidence

ORD record
ord-5042dad116834076bff502d185ccaeaf
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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