Hydrochloric Acid → HCID 10161317, compound

HRID 1064064Notes

Reaction equation

HRID 1064064 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-0bdd96cda3674d2a836061cdcb1937f1
Source dataset
uspto-grants-2005_11
Patent number
US06967208B2

Reaction notes

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