Sodium hydride → HCID 58409950, compound

HRID 1844898Notes

Reaction equation

HRID 1844898 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]3[CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:10]=3O[C:12](=O)[C:13]=2[C:14]#[N:15])[CH2:4][CH2:3]1.[H-].[Na+]>C1COCC1>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]3[CH2:23][C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:10]=3[C:10]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=4[CH2:23][C:12]=3[C:13]=2[C:14]#[N:15])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67395912HCID 67395912, compound

Product 1

HCID 58409950HCID 58409950, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(4-methylpiperidin-1-yl)-2-oxo-2,5-dihydroindeno[1,2-b]pyran-3-carbonitrile (306 mg), indanone-2 (132 mg) and NaH (45 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. White solid; mp 166-168° C.; IR (KBr) 2215 cm−1 (CN); MS (ESI) 377 (M++1).

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-6c90d5b4082e47bbb131ccaa453f7329
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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