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Diisopropylamine → 1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,4-ethynyl-1-[(4-fluorophenyl)methyl]-,ethyl ester

HRID 2377098
Notes
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Reaction equation

HRID 2377098 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](OS(C(F)(F)F)(=O)=O)=[C:8]2[CH:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH:37](NC(C)C)(C)[CH3:38]>CN(C=O)C.[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:37]#[CH:38])=[C:8]2[CH:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 11430Potassium CarbonateHCID 768529391h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-4-[[(trifluoromethyl)sulfonyl]oxy]-,ethyl ester

Product 1

HCID 598558491h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,4-ethynyl-1-[(4-fluorophenyl)methyl]-,ethyl ester

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(4-fluoro-benzyl)-4-trifluoromethanesulfonyloxy-1H-pyrrolo[2,3-c]pyridine -5-carboxylic acid ethyl ester (2.0 g, 4.48 mmol) in DMF (4.5 mL) and diisopropylamine (4.5 mL) was added trimethylsilylalkyne (4.4 mL, 31.4 mmol), copper (I) iodide (68 mg, 0.36 mmol), and bis(triphenylphosphine) palladium (II) chloride (126 mg, 0.18 mmol). The reaction was vacuum degassed with nitrogen three times, and then heated in a pre-heated oil bath at 90° C. After thirty minutes, the reaction was cooled to room temperature and diluted with 20 mL of ethyl acetate. The solution was filtered through a silica plug (15 mm×10 mm), and concentrated. The resulting oil was dissolved in EtOH (25 mL), and potassium carbonate (1.24 g, 9 mmol) was added. The reaction was stirred for 18 hours at room temperature, and then the solids were removed by filtration. The solvent was removed by rotary evaporation, and the resulting residue was dissolved in CH2Cl2 (80 mL). The organic layer was washed with 2×50 mL of water, and then 50 mL of saturated NaCl. After drying the organic liquid over MgSO4, the solids were removed by filtration and then the solvent was removed by rotary evaporation to give the desired product. Yield 0.927 g, 64%. MS (APCI): Calc: 322, Found: (M+H) 323.

Workup

  1. customdegassed with nitrogen three times
  2. waitAfter thirty minutes
  3. temperaturethe reaction was cooled to room temperature
  4. additiondiluted with 20 mL of ethyl acetate
  5. filtrationThe solution was filtered through a silica plug (15 mm×10 mm)
  6. concentrationconcentrated
  7. dissolutionThe resulting oil was dissolved in EtOH (25 mL)
  8. customthe solids were removed by filtration
  9. customThe solvent was removed by rotary evaporation
  10. dissolutionthe resulting residue was dissolved in CH2Cl2 (80 mL)
  11. washThe organic layer was washed with 2×50 mL of water
  12. dry with materialAfter drying the organic liquid over MgSO4
  13. customthe solids were removed by filtration
  14. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-f8d4e741a2c64ddca1fac5b0a44aad74
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07468375B2

Reaction notes

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