Water → HCID 59305024, compound

HRID 2240213Notes

Reaction equation

HRID 2240213 reaction equation
O.O.[Sn](Cl)Cl.[Cl:6][C:7]1[C:15]2[C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:18]=3[F:26])=[CH:13][CH:12]=[N:11][C:10]=2[NH:9][CH:8]=1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][C:14]=2[NH:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=2[F:26])[NH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 59304982HCID 59304982, compound

Product 1

HCID 59305024HCID 59305024, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

147 mg (650 μmol) of tin(II) chloride dihydrate are added to a solution of 40 mg (130 μmol) of 3-chloro-N-(2-fluoro-4-nitrophenyl)-1H-pyrrolo[2,3-b]pyridine-4-amine in 2.50 ml of DMF, and this solution is stirred at RT overnight. 5 ml of water are then added, and the pH is adjusted to 10 using saturated sodium bicarbonate solution. After filtration through Celite, the Celite is washed with 40 ml of ethyl acetate. The aqueous phase of the filtrate is extracted twice with 10 ml of ethyl acetate. The combined organic phases are washed in each case twice with 5 ml of water and 5 ml of saturated sodium chloride solution and dried with sodium sulfate. Concentration under reduced pressure affords the target compound which is reacted further without purification.

Workup

  1. filtrationAfter filtration through Celite
  2. washthe Celite is washed with 40 ml of ethyl acetate
  3. extractionThe aqueous phase of the filtrate is extracted twice with 10 ml of ethyl acetate
  4. washThe combined organic phases are washed in each case twice with 5 ml of water and 5 ml of saturated sodium chloride solution
  5. dry with materialdried with sodium sulfate
  6. concentrationConcentration under reduced pressure
  7. customaffords the target compound which
  8. customis reacted further without purification

Sources & evidence

ORD record
ord-cfe930e7c70f4dd290d6fb3e8e8b6d39
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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