Sodium hydride → HCID 58409920, compound

HRID 1844897Notes

Reaction equation

HRID 1844897 reaction equation
O=[C:2]1O[C:6]2[C:8]3[C:13]([CH2:14][C:5]=2[C:4]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:3]1[C:20]#[N:21])=[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:20]#[N:21])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67394160HCID 67394160, compound

Product 1

HCID 58409920HCID 58409920, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-oxo-4-(pyrrolidin-1-yl)-2,5-dihydroindeno[1,2-b]pyran-3-carbonitrile (278 mg), indanone-2 (132 mg) and NaH (42 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 aid subsequently neutralized with dil. HCl, finally purified by column chromatography using ethylacetate-hexane as eluent. White solid; mp 206-208° C.; 1H NMR (300 MHz, CDCl3) δ 2.03-2.11 (m, 4H, 2CH2), 3.85-3.92 (m, 4H, 2CH2), 4.07 (s, 2H, CH2), 4.11 (s, 2H, CH2), 729-7.35 (m, 1H, ArH), 7.38-7.52 (m, 3H, ArH), 7.58-7.62 (m, 2H, ArH), 8.34 (d, J=7.8 Hz; 1H, ArH), 8.55 (d, J=7.68 Hz, 1H, ArH); IR (KBr) 2213 cm−1 (CN); MS (ESI) 349 (M++1).

Workup

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

Sources & evidence

ORD record
ord-eabf72fea0cf49b38fff490f45e429c7
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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