Dichloromethane → HCID 87192311, compound

HRID 2089027Notes

Reaction equation

HRID 2089027 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[C:15]([Cl:17])[N:14]=[C:13]([NH:18][CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)[CH:12]=3)=[CH:9][N:8]([S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:5]2=[N:6][CH:7]=1.[C:34]1([S:40]([N:43]2[CH:47]=[C:46](B3OC(C)(C)C(C)(C)O3)[CH:45]=[N:44]2)(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.ClCCl.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C.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]>[Cl:17][C:15]1[N:14]=[C:13]([NH:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:12]=[C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:46]4[CH:45]=[N:44][N:43]([S:40]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)(=[O:42])=[O:41])[CH:47]=4)[CH:3]=3)[N:8]([S:25]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)(=[O:27])=[O:26])[CH:9]=2)[CH:16]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 447552031-(Benzenesulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 866498714-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine

Product 1

HCID 87192311HCID 87192311, compoundYield 56.3%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 171a (0.158 g, 0.29 mmol), 1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.100 g, 0.29 mmol), catalytic amount of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane (1:1) and saturated sodium bicarbonate solution (2 mL) in 8 mL dimethylformamide was heated at 65° C. for 2 hours. 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 (20% ethyl acetate/hexane) to afford 0.11 g of the title compound. m/z 673.6 (ESI, M+H)+.

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel using flash chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-67b794a91b3c4ad4967693a19fa83e61
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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