Sodium hydride → HCID 117778137, compound

HRID 1503238Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:16][CH:15]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][O:9][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:18][CH:19]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(6-Chloropyridin-3-yl)methanol (4.3 g) was dissolved in tetrahydrofuran (150 mL), and the solution was cooled to 0° C. Sodium hydride (63%, 1.4 g) was added thereto, and the mixture was stirred at 0° C. for 1 hour. Subsequently, 4′-(bromomethyl)biphenyl-2-carbonitrile (9.0 g) was added thereto at 0° C., and the mixture was stirred at 50° C. for 19 hours. The reaction solution was brought back to room temperature, and a saturated aqueous ammonium chloride solution was added thereto. After extraction with ethyl acetate, the organic layer was dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (Moritex Corporation, elution solvent: hexane/ethyl acetate) to obtain the title compound (6.2 g) as a white solid (yield: 62%).

Workup

stirringat 0° C., and the mixture was stirred at 50° C. for 19 hours
customwas brought back to room temperature
extractionAfter extraction with ethyl acetate
dry with materialthe organic layer was dried over sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (Moritex Corporation, elution solvent: hexane/ethyl acetate)

Sources & evidence

ORD record: ord-a3558e1ab5214f74a6a9d09f089c9a14
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212170B2

Reaction notes

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