Sodium hydride → HCID 58409911, compound

HRID 1844874Notes

Reaction equation

HRID 1844874 reaction equation
O=[C:2]1[C:7]([C:8]#[N:9])=[C:6]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)O1.[H-].[Na+]>>[C:15]1([C:4]2[C:5]3[CH2:4][C:15]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:2]=3[C:7]([C:8]#[N:9])=[C:6]([N:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)[CH:5]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 24758Sodium hydrideHCID 111292452H-Pyran-3-carbonitrile, 2-oxo-6-phenyl-4-(1-pyrrolidinyl)-

Product 1

HCID 58409911HCID 58409911, compound

Procedure

A mixture of 2-oxo-6-phenyl-4-(pyrrolidin-1-yl)-2H-pyran-3-carbonitrile (266 mg), indanone-1 (132 mg) and NaH (31 mg) in THIF 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 158-160° C.; ESIMS 336 (M+); IR (KBr) 2203 cm−1 (CN); 1H NMR (200 MHz, CDCl3) δ 2.01-2.05 (m, 4H, 2CH2), 3.68-3.72 (m, 4H, 2CH2), 3.78 (s, 2H, CH2), 6.63 (s, 1H, ArH), 7.30-7.51 (m, 8H, ArH), 8.63 (d, J=7.8 Hz, 1H, ArH); HRMS calcd. for C24H20N2 336.1627. Found 336.1599.

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-958769094b9f40f0866e4c24c153ae46
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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