(Diethylamino)sulfur trifluoride → HCID 68644476, compound

HRID 1158932Notes

Reaction equation

[C:1]([C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[C:10]([CH2:26]O)=[C:11]([CH2:16][NH:17][C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)[CH:12]=[N:13][C:14]=2[CH3:15])=[CH:5][CH:4]=1)#[N:2].C(N(S(F)(F)[F:36])CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[C:10]([CH2:26][F:36])=[C:11]([CH2:16][NH:17][C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)[CH:12]=[N:13][C:14]=2[CH3:15])=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of 4-{[5-(4-cyano-benzyloxy)-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl]-amino}-benzonitrile (8) (1765 mg, 4.60 mmol) in dry dichloromethane (200 mL) was slowly added diethylaminosulfurtrifluoride (DAST) (741 mg, 4.6 mmol) in dry dichloromethane (50 mL) at −78° C. under nitrogen atmosphere. The reaction temperature was warmed to −40° C. and stirred for 30 minutes. The reaction mixture was then poured into a cold solution of saturated aqueous sodium bicarbonate, and the crude product was extracted with dichloromethane, washed with water, and dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude residue, which was purified by column chromatography on silica gel using dichloromethane:hexane:methyl alcohol (15:10:1) as an eluant to give 4-{[5-(4-cyano-benzyloxy)-4-fluoromethyl-6-methyl-pyridin-3-ylmethyl]-amino}-benzonitrile (10) (650 mg, 37% yield) as a colorless solid.

Workup

customat −78° C.
extractionthe crude product was extracted with dichloromethane
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
customEvaporation of the solvent
customgave a crude residue, which
customwas purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-9e2af2497a184097984191d131cd8618
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812037B2

Reaction notes

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