Sodium hydride → HCID 66747768, compound

HRID 1622847

Reaction equation

[H-].[Na+].[NH2:3][C:4]1[C:9]([O:10][C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([OH:21])=[CH:18]3)=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][N:5]=1.CC1C=CC(S(O[CH2:33][C:34]([F:37])([F:36])[F:35])(=O)=O)=CC=1.[Cl-].[NH4+]>CS(C)=O.C1COCC1>[F:35][C:34]([F:37])([F:36])[CH2:33][O:21][C:17]1[CH:18]=[C:19]2[C:14]([CH:13]=[CH:12][C:11]([O:10][C:9]3[C:4]([NH2:3])=[N:5][CH:6]=[CH:7][CH:8]=3)=[CH:20]2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of sodium hydride (60%, 116 mg), 7-[(2-aminopyridin-3-yl)oxy]naphthalen-2-ol (477 mg) and dehydrated THF (10 mL) was added a mixture of 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (370 mg) and dehydrated THF (5 mL) at room temperature. The reaction mixture was stirred at 70° C. over the weekend, DMSO (10.00 mL) was added and the mixture was stirred at 120° C. for 1 hr. The reaction mixture was added to a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (82 mg) as a pale-yellow viscous product.

Workup

additionwas added
additionwas added
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-bf8688a6dd884773b760b53cec52ab19
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778934B2

Linked notes

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