Sodium hydride → HCID 86695952, compound

HRID 2369555Notes

Reaction equation

HRID 2369555 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-87c571c24cfb4d04b14a652f475329d0
Source dataset
uspto-grants-2014_04
Patent number
US08703953B2

Reaction notes

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