Dichloromethane → HCID 86722832, compound

HRID 1778722Notes

Reaction equation

HRID 1778722 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19]([CH:28]=[CH2:29])=[N:20][N:21]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[C:15]=2[CH:14]=1.I[C:31]1[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=1.[OH-].[Ba+2].[OH-].ClCCl>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19](/[CH:28]=[CH:29]/[C:31]3[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=3)=[N:20][N:21]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[C:15]=2[CH:14]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 27347731-Methyl-4-iodo-1H-pyrazoleHCID 6093286Barium hydroxideHCID 86722831HCID 86722831, compound

Product 1

HCID 86722832HCID 86722832, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-3-vinyl-1H-pyrazolo[4,3-c]pyridine (0.1 mmol) in N,N-dimethylformamide (0.5 mL) was added 4-iodo-1-methyl-1H-pyrazole (22 mg, 0.10 mmol) (Aldrich Cat. No. 683531), barium hydroxide (36 mg, 0.21 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (5.6 mg, 0.0069 mmol), and water (0.05 mL). The mixture was degassed and sealed. The mixture was stirred at 95° C. overnight. After cooling the solid was filtered off, washed with acetonitrile. The filtrate was concentrated under reduced pressure to afford the crude product which was directly used in next step reaction without further purification. LCMS (M+H)+=514.2/516.1.

Workup

  1. customThe mixture was degassed
  2. customsealed
  3. temperatureAfter cooling the solid
  4. filtrationwas filtered off
  5. washwashed with acetonitrile
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5fe34dd1d30843deaee0502494e78cf0
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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