4-Toluenesulfonyl chloride → HCID 11528667, compound

HRID 1712106Notes

Reaction equation

HRID 1712106 reaction equation
O[CH:2]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[CH2:17][OH:18])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].S(Cl)(C1C=CC(C)=CC=1)(=O)=O.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[CH:2]1([C:3]2[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=2)[C:6]#[N:7])[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[CH2:17][O:18]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 59205176HCID 59205176, compound

Product 1

HCID 11528667HCID 11528667, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[Hydroxy-(3-hydroxymethyl-pyridin-4-yl)-methyl]-benzonitrile (100 mg, 0.42 mmol) and tosyl chloride (96 mg, 0.50 mmol) were dissolved in dichloromethane (5 mL) and then the reaction mixture was treated with triethylamine (0.09 mL, 0.65 mmol). The reaction mixture was stirred overnight at room temperature, then diluted with ethyl acetate and washed with 5% sodium bicarbonate. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by chromatography of silica gel with 30% ethyl acetate in hexane to yield 3-(1,3-dihydro-furo[3,4-c]pyridin-1-yl)-benzonitrile as a white solid.

Workup

  1. washwashed with 5% sodium bicarbonate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe residue purified by chromatography of silica gel with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6833ba9807e74383a9f9b6f7fe07321e
Source dataset
uspto-grants-2010_09
Patent number
US07790895B2

Reaction notes

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