1,4-Cyclohexadiene → 3-(6-Fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-5-(tetrahydro-2H-pyran-3-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1774991Notes

Reaction equation

HRID 1774991 reaction equation
[O:1]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[N:17]=4)=[N:14][N:13]([CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][O:24]4)[C:10]3=[CH:11][N:12]=2)[CH2:4][CH2:3][CH2:2]1.C1CC=CCC=1>[Pd].C(O)C>[F:22][C:18]1[N:17]=[C:16]([C:15]2[C:9]3[C:10](=[CH:11][N:12]=[C:7]([CH:5]4[CH2:4][CH2:3][CH2:2][O:1][CH2:6]4)[CH:8]=3)[N:13]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][O:24]3)[N:14]=2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 712537765-(3,4-Dihydro-2H-pyran-5-yl)-3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 712536873-(6-Fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-5-(tetrahydro-2H-pyran-3-yl)-1H-pyrazolo[3,4-c]pyridineYield 101.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 68 mg (0.18 mmol) of 5-(3,4-dihydro-2H-pyran-5-yl)-3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine, 2.0 ml (21 mmol) of 1,4-cyclohexadiene and 300 mg of 10% palladium on carbon in 8 ml of ethanol was heated to reflux for 24 hours. The mixture was filtered through celite, the filtrate concentrated in vacuum to afford 70 mg (100%) of 3-(6-Fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-5-(tetrahydro-2H-pyran-3-yl)-1H-pyrazolo[3,4-c]pyridine. ESI MS m/z 383.1 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. filtrationThe mixture was filtered through celite
  4. concentrationthe filtrate concentrated in vacuum

Sources & evidence

ORD record
ord-9e7ce0e8c994421abe0024c6b08fdc3c
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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