Sodium hydride → HCID 86695952, compound

HRID 870963Notes

Reaction equation

HRID 870963 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([CH3:14])[C:9]=2[CH2:15][OH:16])=[C:4](F)[CH:3]=1.[H-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9](=[C:10]([CH3:14])[N:11]=[CH:12][CH:13]=3)[CH2:15][O:16][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86695951(4-(4-Chloro-2-fluorophenyl)-2-methylpyridin-3-yl)methanol

Product 1

HCID 86695952HCID 86695952, compoundYield 170.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-(4-chloro-2-fluorophenyl)-2-methylpyridin-3-yl)methanol (70 mg, 0.278 mmol) in tetrahydrofuran (3 mL) at 0° C. was added NaH (33.4 mg, 0.834 mmol) portionwise. The solution was allowed to warm to room temperature and stirred for 5 h. The reaction mixture was quenched with ice cold water and diluted with EtOAc (15 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to afford 8-chloro-4-methyl-5H-chromeno[3,4-c]pyridine (0.11 g, 0.475 mmol, 73% yield) as a brown solid. LCMS (ESI) m/e 232.00 [(M+H)+, calcd for C13H12ClNO 232.01]; LC/MS retention time (Method G): tR=1.00 min.

Workup

  1. customThe reaction mixture was quenched with ice cold water
  2. additiondiluted with EtOAc (15 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6587e57644534bd380ce99d36e4d3529
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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