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Ethanol → Ethyl 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxylate

HRID 1253534
Notes
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Reaction equation

HRID 1253534 reaction equation
I[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[CH:8]=[C:7]([O:17][CH3:18])[C:6]=12.CC1(C)C2[C:41](=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)[O:40][C:22]2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=C[C:21]1=2.C(N(CC)CC)C.C([OH:70])C>[Pd](Cl)Cl>[CH3:18][O:17][C:7]1[C:6]2[N:5]([N:4]=[CH:3][C:2]=2[C:41]([O:40][CH2:22][CH3:21])=[O:70])[CH:10]=[C:9]([C:11]2[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=2)[CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 448167683-iodo-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

Product 1

HCID 67374371Ethyl 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxylate

Reagents, catalysts & solvents

1
HCID 24290Palladium ChlorideCatalyst

Conditions

Temperature
100 °C

Procedure

3-iodo-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine (650.0 mg, 1.835 mmol), palladium (II) chloride (16.3 mg, 0.092 mmol), and Xantphos (53.1 mg, 0.092 mmol) were placed in a 40 mL scintillation vial. Absolute ethanol (6 ml) and triethylamine (0.384 ml, 2.75 mmol) were added and the mixture was sparged with argon for 5 minutes. The vial was transferred to a pressure reactor, which was filled with CO (30 psi) and vented (3×). The vessel was pressurized to 100 psi of CO and heated to 100° C. After 4 h, the system was cooled to ambient temperature. The reaction mixture was diluted in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and brine then dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient) to give ethyl 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxylate.

Workup

  1. customthe mixture was sparged with argon for 5 minutes
  2. customThe vial was transferred to a pressure reactor
  3. additionwhich was filled with CO (30 psi)
  4. temperaturethe system was cooled to ambient temperature
  5. additionThe reaction mixture was diluted in ethyl acetate
  6. washwashed with saturated aqueous sodium hydrogen carbonate and brine
  7. dry with materialthen dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient)

Sources & evidence

ORD record
ord-815f5d1cfb124e49bec1c7c1311e1eb2
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08455477B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes