Sodium hydride → HCID 58409907, compound

HRID 1844899Notes

Reaction equation

HRID 1844899 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[C:23]2[C:6]([CH2:7][C:8]3[C:13]([N:14]4[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]4)=[C:12]([C:20]#[N:21])[C:11](=O)O[C:9]=32)=[CH:5][CH:4]=1.[H-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[CH2:7][C:8]3[C:13]([N:14]4[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]4)=[C:12]([C:20]#[N:21])[C:11]4[CH2:7][C:6]5[CH:5]=[CH:4][CH:3]=[CH:24][C:23]=5[C:9]=4[C:9]=3[C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67394083HCID 67394083, compound

Product 1

HCID 58409907HCID 58409907, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8-methoxy-2-oxo-4-(piperidin-1-yl)-2,5-dihydroindeno[1,2-b]pyran-3-carbonitrile (322 mg), indanone-2 (132 mg) and NaH (39 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 180-182° C.; IR (KBr) 2212 cm−1 (CN); MS (ESI) 393 (M++1); 13C NMR (150 MHz, CDCl3) δ 26.22, 35.46, 38.54, 51.70, 94.61, 119.87, 122.42, 122.68, 124.68, 124.79, 127.09, 127.17, 127.64, 127.77, 129.66, 132.09, 139.48, 140.39, 142.58, 144.25, 144.40, 144.54, 149.42.

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-e76f51db35724427b1e169fc2e2850bb
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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