Sodium hydride → HCID 58409932, compound

HRID 1844893Notes

Reaction equation

HRID 1844893 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:3]([C:21]#[N:22])=[C:2]3[C:5]([CH2:6][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=43)=[C:6]3[C:8]4[C:13]([CH2:14][C:5]=23)=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67393714HCID 67393714, compound

Product 1

HCID 58409932HCID 58409932, 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-1 (132 mg) and NaH (41 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 186-188° C.; 1H NMR (200 MHz, CDCl3) δ 1.66-1.70 (m, 2H, CH2), 1.81-1.85 (m, 2H, CH2), 3.34-3.42 (m, 4H, CH2), 4.11 (s, 2H, CH2), 4.17 (s, 2H, CH2), 7.40-7.46 (m, 4H, ArH), 7.60-7.68 (m, 2H, ArH), 7.92 (d, 1H, J=7.8 Hz, ArH), 8.52 (d, 1H, J=7.5 Hz, ArH); MS (ESI) 363 (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-fc12568f3a3346f2bd72dd091fcfb957
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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