Water → HCID 86722833, compound

HRID 1778725Notes

Reaction equation

HRID 1778725 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]([CH2:36][CH2:37][O:38][CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][O:40]2)[CH:35]=1.ClCCl.O>CN(C=O)C.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]>[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]([CH2:36][CH2:37][O:38][CH:39]4[CH2:44][CH2:43][CH2:42][CH2:41][O:40]4)[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

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 593418524-Iodo-1-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)-1H-pyrazoleHCID 86722831HCID 86722831, compound

Product 1

HCID 86722833HCID 86722833, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 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 DMF (0.5 mL) was added 4-iodo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1H-pyrazole (44 mg, 0.14 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (7.5 mg, 0.0092 mmol), and water (0.05 mL). The mixture was degassed and sealed. It was stirred at 95° C. for 3 h. After cooling the solid was filtered off, washed with acetonitrile. The filtrate 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 (32 mg). LCMS (M+H)+=628.2/630.3.

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
  7. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-23cd000d3ec2443cbe1fe8b18d1a8a10
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

Loading…