Sodium hydride → HCID 86646258, compound

HRID 1514749Notes

Reaction equation

HRID 1514749 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:14]([CH2:15][OH:16])=[C:13](/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:12][N:11]=2)=[N:8][CH:9]=1.Cl[C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][N:27]=1.[Cl-].[NH4+]>C1COCC1.O>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:14]([CH2:15][O:16][C:26]3[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][N:27]=3)=[C:13](/[CH:17]=[CH:18]/[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[O:12][N:11]=2)=[N:8][CH:9]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 66718156HCID 66718156, compound

Product 1

HCID 86646258HCID 86646258, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of sodium hydride (129 mg, 3.22 mmol) in THF (4.5 mL) was added a solution of (E)-(3-(5-fluoropyridin-2-yl)-5-styrylisoxazol-4-yl)methanol (866 mg, 2.92 mmol) in THF (9 mL) at room temperature. The reaction mixture was stirred for 1 h at room temperature. A solution of methyl 6-chloronicotinate (602 mg, 3.51 mmol) in THF (9 mL) was added. The reaction was stirred at room temperature overnight and water (150 mL) and saturated aqueous ammonium chloride solution (100 mL) were added. Extraction with ethyl acetate and chromatography (silica, ethyl acetate:heptane=1:9 to 2:3) afforded the title compound (906 mg, 66%) as a white solid. MS: m/e=432.2 [M+H]+.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. extractionExtraction with ethyl acetate and chromatography (silica, ethyl acetate:heptane=1:9 to 2:3)

Sources & evidence

ORD record
ord-39e3e65bd31e4897845132300bb3aead
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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