Sodium hydride → HCID 58409915, compound

HRID 1844896Notes

Reaction equation

HRID 1844896 reaction equation
O=[C:2]1O[C:6]2[C:8]3[C:13]([CH2:14][C:5]=2[C:4]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:3]1[C:21]#[N:22])=[CH:12][CH:11]=[CH:10][CH:9]=3.[H-].[Na+]>C1COCC1>[N:15]1([C:4]2[C:5]3[CH2:14][C:13]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[C:6]=3[C:6]3[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=4[CH2:14][C:2]=3[C:3]=2[C:21]#[N:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67393714HCID 67393714, compound

Product 1

HCID 58409915HCID 58409915, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-oxo-4-(piperidin-1-yl)-2,5-dihydroindeno[1,2-b]pyran-3-carbonitrile (292 mg), indanone-2 (132 mg) and NaH. (40 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 200-202° C.; IR (KBr) 2215 cm−1 (CN); MS (ESI) 363 (M++1) HRMS Calculated for C26H22N2 362.1783 measured 362.1792.

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-00763c0311e041dbb6cd5e05a1113461
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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