Dichloromethane → 4-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine

HRID 2089026Notes

Reaction equation

HRID 2089026 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.Cl[CH2:22][Cl:23].C(=O)(O)[O-].[Na+].C(O[CH2:33][CH3:34])(=O)C>CN(C)C=O.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:3]3[CH:2]=[C:22]([Cl:23])[N:6]=[C:5]([NH:8][CH:34]4[CH2:33][CH2:17][CH2:16][CH2:15][CH2:20]4)[CH:4]=3)=[CH:9][N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 242292401-Benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 866498714-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.155 g, 2.49 mmol), Example 168a (0.924 g, 2.74 mmol), catalytic amount of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane (1:1) and saturated sodium bicarbonate solution (6 mL) in 24 mL dimethylformamide was heated at 65° C. for 30 minutes. The material was cooled to room temperature, diluted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified on silica gel using flash chromatography (6% ethyl acetate/hexane) to afford 0.68 g of the title compound. m/z 547.4 (APCI, M+H)+.

Workup

  1. customwas heated at 65° C. for 30 minutes
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel using flash chromatography (6% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2d027f35779b451cbfd67127525f9c7d
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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