Hydrochloric Acid → HCID 10161317, compound

HRID 890544Notes

Reaction equation

HRID 890544 reaction equation
Br[C:2]1[C:10]2[CH2:9][CH2:8][N:7]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]4=[O:23])=[CH:13][CH:12]=3)[C:6](=[O:24])[C:5]=2[N:4]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[N:3]=1.[Li+].[Cl-].Cl.C1C[O:39][CH2:38][CH2:37]1>>[C:38]([C:2]1[C:10]2[CH2:9][CH2:8][N:7]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]4=[O:23])=[CH:13][CH:12]=3)[C:6](=[O:24])[C:5]=2[N:4]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[N:3]=1)(=[O:39])[CH3:37]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 433294Lithium ChlorideHCID 22240527HCID 22240527, compound

Product 1

HCID 10161317HCID 10161317, compound

Procedure

To 3-bromo-1-(4-methoxy-phenyl)-6-[4-(2-oxo-2H-pyridin-1-yl)-phenyl]-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one (0.11 g, 0.22 mmol) was added THF (25 mL), 1-(ethoxyvinyl)tributyltin (0.078 mL, 0.23 mmol), and LiCl (27 mg, 0.65 mmol) and the mixture was degassed with N2 for 15 min. Tetrakistriphenylphosphine Palladium(0) (12 mg, 0.01 mmol) was added and the reaction was heated to reflux 24 h. The reaction was cooled to rt and treated with 1N HCl for 24 h. After extraction with EtOAc and drying (MgSO4), the product was purified by silica gel (mixed with KF) chromatography using 0–3% MeOH in CH2Cl2 and by HPLC to afford 6 mg (6%); High Resolution Mass Spec (M+H)+ for C26H23N4O4 455.1713.

Workup

  1. customthe mixture was degassed with N2 for 15 min
  2. temperaturethe reaction was heated
  3. temperatureto reflux 24 h
  4. extractionAfter extraction with EtOAc
  5. dry with materialdrying (MgSO4)
  6. customthe product was purified by silica gel (mixed with KF) chromatography
  7. customby HPLC to afford 6 mg (6%)

Sources & evidence

ORD record
ord-392461d1dbb04f7a81778dabf1f71ff6
Source dataset
uspto-grants-2006_02
Patent number
US06995172B2

Reaction notes

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