Hydrochloric Acid → HCID 117778047, compound

HRID 1500506Notes

Reaction equation

HRID 1500506 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[CH:4][N:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.C[Si]([N-:52][Si](C)(C)C)(C)C.[Li+].Cl.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:17]1([C:14]2[CH:15]=[CH:16][C:11]([CH2:10][O:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([NH2:52])=[N:3][CH:4]=3)=[CH:12][CH:13]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2733832Lithium HexamethyldisilazideHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 117778019HCID 117778019, compound

Product 1

HCID 117778047HCID 117778047, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-chloro-5-[(4-phenylphenyl)methoxymethyl]pyridine (0.206 g) in tetrahydrofuran (10 mL), tris(dibenzylideneacetone)dipalladium (63 mg), 2-(dicyclohexylphosphino)biphenyl (48 mg), and a solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1.0 M, 1.0 mL) were added at room temperature, and the mixture was heated to reflux for 22 hours under a nitrogen atmosphere. Hydrochloric acid (2 M, 10 mL) was added to the reaction solution, and the mixture was further stirred for 30 minutes. The reaction solution was cooled to room temperature, and sodium carbonate was gradually added thereto, and subsequently, water was added thereto, followed by extraction with dichloromethane. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column (Yamazen Corporation, elution solvent: dichloromethane/methanol) to obtain the title compound (0.189 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 22 hours under a nitrogen atmosphere
  3. extractionfollowed by extraction with dichloromethane
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by chromatography on a silica gel column (Yamazen Corporation, elution solvent: dichloromethane/methanol)

Sources & evidence

ORD record
ord-0acdfb12906340769a29ab4a5df22c1b
Source dataset
uspto-grants-2015_12
Patent number
US09206168B2

Reaction notes

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