Water → 1-(benzenesulfonyl)-2-ethynyl-1H-pyrrolo[2,3-b]pyridine

HRID 2196731Notes

Reaction equation

HRID 2196731 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([S:13]([N:16]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH:18]=[C:17]2[CH:25]=O)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N+](=[C:29](P(=O)(OC)OC)C(=O)C)=[N-].O>CO.C(OCC)(=O)C>[C:25]([C:17]1[N:16]([S:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:15])=[O:14])[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[CH:18]=1)#[CH:29]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 566921991-(Phenylsulfonyl)-1H-pyrrolo(2,3-b)pyridine-2-carboxaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 730135321-(benzenesulfonyl)-2-ethynyl-1H-pyrrolo[2,3-b]pyridineYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.97 g, 6.98 mmol) was added to a suspension of 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (1.00 g, 3.49 mmol) in methanol (1.0 mL), followed by the addition of a solution of dimethyl 1-diazo-2-oxopropylphosphonate (0.81 g, 4.19 mmol) in methanol (0.2 mL). The reaction mixture was stirred at room temperature for 2 hours, after which water was added, then ethyl acetate. The layers were separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude was purified by flash chromatography to afford 2-ethynyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.40 g, 41%; purity 70%).

Workup

  1. customThe layers were separated
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. dry with materialThe organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-5e9e552f5a58458693df8b5aebb59c50
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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