(Diethylamino)sulfur trifluoride → HCID 68644248, compound

HRID 1158935Notes

Reaction equation

HRID 1158935 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][O: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].CCN(S(F)(F)[F:36])CC.C(=O)(O)[O-].[Na+]>ClCCl>[F:36][CH2:26][C:10]1[C:9]([O:8][CH2:7][C:6]2[CH:28]=[CH:29][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[C:14]([CH3:15])[N:13]=[CH:12][C:11]=1[CH2:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 68644473HCID 68644473, compound

Product 1

HCID 68644248HCID 68644248, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-(4-cyano-benzyloxy)-4-hydroxymethyl-6-methyl-pyridin-3-ylmethoxy)-benzonitrile (14) (600 mg, 1.6 mmol) in dry dichloromethane (20 mL) was slowly added DAST (251 mg, 1.6 mmol, in 50 mL dry dichloromethane) at −78° C. under nitrogen atmosphere. The reaction mixture was warmed to room temperature and stirred for 3 hours. The reaction mixture was then poured into a cold solution of saturated aqueous sodium bicarbonate, and the crude product extracted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude residue, which was purified by column chromatography on silica gel using ethyl acetate:hexane:methyl alcohol (7:7:1) as an eluant to give 4-[4-fluoromethyl-6-methyl-5-(4-cyano-benzyloxy)-pyridin-3-ylmethoxy]-benzonitrile (18) (314 mg, 52% yield) as a colorless solid.

Workup

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

Sources & evidence

ORD record
ord-c18a832ad1994c1cb4cbc37f88f87e2e
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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