Sodium hydride → HCID 117778019, compound

HRID 1500505Notes

Reaction equation

HRID 1500505 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:16][CH:15]=2)=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 177161(6-Chloropyridin-3-yl)methanolHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-

Product 1

HCID 117778019HCID 117778019, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (6-chloro-3-pyridyl)methanol (0.538 g) in tetrahydrofuran (15 mL), sodium hydride (63% oil, 0.182 g) was added at 0° C., and the mixture was stirred at room temperature for 30 minutes. 1-(Bromomethyl)-4-phenylbenzene (0.932 g) was added to the reaction solution at room temperature, and the mixture was stirred at 50° C. for 3 hours. The reaction solution was cooled to 0° C., and a saturated aqueous ammonium chloride solution 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: hexane/ethyl acetate) to obtain the title compound (0.896 g).

Workup

  1. stirringthe mixture was stirred at 50° C. for 3 hours
  2. temperatureThe reaction solution was cooled to 0° C.
  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: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-34c981f7049f4284855ad070c67de98a
Source dataset
uspto-grants-2015_12
Patent number
US09206168B2

Reaction notes

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