Sodium hydride → HCID 9966806, compound

HRID 1743908Notes

Reaction equation

HRID 1743908 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:13]=[C:12]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:11]2[C:6](=[CH:7][C:8]([CH2:19][OH:20])=[CH:9][CH:10]=2)[N:5]=1.Cl.Cl[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1>>[CH3:3][C:4]1[CH:13]=[C:12]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:11]2[C:6](=[CH:7][C:8]([CH2:19][O:20][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[CH:9][CH:10]=2)[N:5]=1

Participants

4

Reactant 3

HCID 24758Sodium hydride2×HCID 818524-Chloropyridine hydrochloride2×HCID 11195876HCID 11195876, compound

Product 1

HCID 9966806HCID 9966806, compoundYield 24.4%

Conditions

Temperature
90 °C

Procedure

Sodium hydride (55–65% dispersion in mineral oil, 40 mg, 1.0 mmol) was added to a mixture of (2-methyl-4-pyrrolidin-1-yl-quinolin-7-yl)-methanol (example 2, 100 mg, 0.41 mmol) and 4-chloropyridine hydrochloride (62 mg, 0.41 mmol), and the mixture was heated at 90° C. for 18 h. Then another portion of sodium hydride (40 mg) and 4-chloropyridine hydrochloride (62 mg) was added, and stirring at 90° C. was continued for 24 h. After cooling, the reaction mixture was partitioned between 1 M aq. sodium carbonate solution and ethyl acetate. The organic layer was separated, washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, dichloromethane/methanol 9:1) afforded the title compound (32 mg, 24%). Yellow solid, ISP-MS: m/e=320.4 ([M+H]+).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between 1 M aq. sodium carbonate solution and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-89e16e8780564bb998fcd35b732d10a9
Source dataset
uspto-grants-2006_03
Patent number
US07012073B2

Reaction notes

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