Dichloromethane → HCID 86722818, compound

HRID 1778690Notes

Reaction equation

HRID 1778690 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:4]=2[CH:3]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:22]=[C:23]([O:25][CH3:26])[CH:24]=1.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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]>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:2]2[N:7]=[CH:6][C:5]3[CH:8]=[N:9][N:10]([CH:11]4[CH2:16][CH2:15][CH2:14][CH2:13][O:12]4)[C:4]=3[CH:3]=2)[CH:22]=[C:23]([O:25][CH3:26])[CH:24]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 162176602-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 714636356-Chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 86722818HCID 86722818, compoundYield 57.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine (0.80 g, 3.4 mmol) (Example 24, Step 1), 2-(3,5-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.1 g, 4.0 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (200 mg, 0.3 mmol), and potassium phosphate (1400 mg, 6.7 mmol) in 1,4-dioxane (7 mL) and water (1 mL) in a reaction vial was degassed and sealed. It was stirred at 90° C. for 2 h. After cooling it was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (660 mg). LCMS (M+H)+=340.1.

Workup

  1. customvial was degassed
  2. customsealed
  3. temperatureAfter cooling it
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-e2d6d3ea918c4598993f8dfebd2cd518
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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