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Hydrochloric Acid → 2-[(3-Acetyl-4-pyridyl)methyl]-6-methoxy-tetralin-1-one

HRID 2207198
Notes
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Reaction equation

HRID 2207198 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]1=[O:21].[CH2:22]([O:24]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:23].Cl>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:22]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]1=[O:21])(=[O:24])[CH3:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 1185580372-[(3-Bromo-4-pyridyl)methyl]-6-methoxy-tetralin-1-one

Product 1

HCID 1185580142-[(3-Acetyl-4-pyridyl)methyl]-6-methoxy-tetralin-1-oneYield 96%

Reagents, catalysts & solvents 3

HCID 11776Triphenylphosphine
Catalyst
HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalyst
HCID 1140TolueneSolvent2×

Conditions

Temperature
110 °C

Procedure

A toluene solution (9 mL) of compound 99 (1.0 g, 2.89 mmol), Pd(dba)2 (70 mg, 0.12 mmol) and PPh3 (30 mg, 0.12 mmol) was stirred at room temperature under argon for 15 min. Then, (1-ethoxyvinyl)tri(n-butyl)stannane (1.08 mL, 3.18 mmol) in toluene (6 mL) was added and the resulting mixture was stirred overnight at 110° C., cooled to room temperature and filtered on Celite, washed with EtOAc and concentrated under reduced pressure. Purification on silica gel (Petroleum ether 100% to EtOAc 100%) afford the product which was placed in presence of an aqueous solution of HCl 1M for 30 minutes at room temperature. After neutralization with a saturated aqueous solution of NaHCO3, aqueous phase was extracted with dichloromethane and the combined organic layers were dried over magnesium sulfate to afford the title compound 103 (Yield 475 mg, 96%) which was used without further purification.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered on Celite
  3. washwashed with EtOAc
  4. concentrationconcentrated under reduced pressure
  5. customPurification on silica gel (Petroleum ether 100% to EtOAc 100%)
  6. customafford the product which
  7. extractionAfter neutralization with a saturated aqueous solution of NaHCO3, aqueous phase was extracted with dichloromethane
  8. dry with materialthe combined organic layers were dried over magnesium sulfate

Sources & evidence

ORD record
ord-15fcde66a99b4ee0bc4565b75a632c25
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09376387B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes