Sodium hydride → 8-chloro-2-methyl-5H-chromeno[3,4-c]pyridine

HRID 870977Notes

Reaction equation

HRID 870977 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10][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](=[CH:10][N:11]=[C:12]([CH3:14])[CH:13]=3)[CH2:15][O:16][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86695959(4-(4-Chloro-2-fluorophenyl)-6-methylpyridin-3-yl)methanol

Product 1

HCID 866959608-chloro-2-methyl-5H-chromeno[3,4-c]pyridineYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (4-(4-chloro-2-fluorophenyl)-6-methylpyridin-3-yl)methanol (0.25 g, 0.993 mmol) in tetrahydrofuran (25 mL) at 0° C. was added NaH (0.06 g, 1.49 mmol) portionwise. The solution was then stirred for 16 h at RT. The reaction mixture was quenched with water (100 mL). The precipitate was collected by filtration and air dried to afford 8-chloro-2-methyl-5H-chromeno[3,4-c]pyridine (0.2 g, 0.863 mmol, 69% yield) as a white solid. LCMS (ESI) m/e 232.0 [(M+H)+, calcd for C13H11ClNO 232.0]; LC/MS retention time (Method D): tR=2.06 min; 1H NMR (400 MHz, CDCl3) δ 8.31 (s, 1H), 7.65 (d, J=4.40 Hz, 1H), 7.37 (s, 1H), 7.07-7.03 (m, 2H), 5.14 (s, 2H), 2.61 (s, 3H).

Workup

  1. customThe reaction mixture was quenched with water (100 mL)
  2. filtrationThe precipitate was collected by filtration and air
  3. customdried

Sources & evidence

ORD record
ord-163441b3d77b499cba28b203fb11015e
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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