Tetrahydrofuran → HCID 58409931, compound

HRID 1844890Notes

Reaction equation

HRID 1844890 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3O[C:16](=O)[C:15]([C:19]#[N:20])=[C:14]([N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)[CH:13]=3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.[H-].[Na+].[CH2:29]1[CH2:33]O[CH2:31][CH2:30]1>>[N:21]1([C:14]2[CH:13]=[C:12]([C:9]3[CH:10]=[CH:11][C:6]([N:1]4[CH:5]=[CH:4][CH:3]=[CH:2]4)=[CH:7][CH:8]=3)[C:5]3[C:4]4[C:30](=[CH:29][CH:33]=[CH:2][CH:3]=4)[CH2:31][C:16]=3[C:15]=2[C:19]#[N:20])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 67395214HCID 67395214, compound

Product 1

HCID 58409931HCID 58409931, compound

Procedure

A mixture of 6-(4-(1H-pyrrol-1-yl)phenyl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile (345 mg), indanone-2 (132 mg) and NaH (47 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 224-226° C.; ESMS 416 (M++1); IR (KBr) 2211 cm−1 (CN); 1H NMR (200 MHz, CDCl3) δ 1.60-1.66 (m, 2H, CH2), 1.79-1.82 (m, 4H, 2CH2), 3.22-3.30 (m, 4H, 2CH2) δ 6.42 (t, J=2 Hz, 2H, CH), 6.82 (s, 1H, ArH), 6.93 (d, J=7.8 Hz, 1H, ArH), 7.07 (t, J=7.5 Hz, 1H, ArH), 7.17-7.24 (m; 4H, ArH & CH), 7.46-7.59 (m, 4H, ArH).

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-1d17a8fdd07641c19a5fa532afce4e32
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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