Sodium hydride → HCID 58409938, compound

HRID 1844878Notes

Reaction equation

HRID 1844878 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2O[C:12](=O)[C:11]([C:15]#[N:16])=[C:10]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH2:8][C:5]4[C:4](=[CH:3][CH:2]=[CH:7][CH:6]=4)[C:12]=3[C:11]([C:15]#[N:16])=[C:10]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 668842646-(4-Fluorophenyl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile

Product 1

HCID 58409938HCID 58409938, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-(4-fluorophenyl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile (298 mg), indanone-1 (132 mg) and NaH (36 mg) in THF was stirred for <5 min. After completion, the reaction solvent was evaporated under vacuum to dryness and crude solid was quenched with ice water and subsequently neutralized with dil. HCl, finally purified by column chromatography using ethylacetate-hexane as eluent. Yellow solid; mp 176-178° C.; FAB MS 368 (M+); IR (KBr) 2220 cm−1 (CN); HRMS calcd. for C25H21FN2 368.16888. Found 368.16806.

Workup

  1. customAfter completion, the reaction solvent was evaporated under vacuum to dryness
  2. customcrude solid was quenched with ice water
  3. customfinally purified by column chromatography

Sources & evidence

ORD record
ord-5f5105c917044bb89e8718d66a812be5
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

Loading…