Dimethyl Sulfate → tert-butyl 6-methoxy-8-phenylsulfonyl-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

HRID 2179348Notes

Reaction equation

HRID 2179348 reaction equation
[OH:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C:10]=3[C:6]=2[CH:5]=[C:4]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:3]=1.[C:31](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>CC(C)=O>[CH3:31][O:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[CH2:11][C:10]=3[C:6]=2[CH:5]=[C:4]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:23])=[O:24])[CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 68108520tert-butyl 6-hydroxy-8-phenylsulfonyl-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

Product 1

HCID 68109569tert-butyl 6-methoxy-8-phenylsulfonyl-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 85.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the product of step A (470 mg, 1.06 mmol) in acetone (45 mL) under a nitrogen atmosphere was added potassium carbonate (1.34 g, 9.7 mmol) and dimethylsulfate (0.22 mL, 2.11 mmol). The reaction mixture was refluxed for 2 h, cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo and the residue purified by column chromatography (SiO2, 8:2, hexanes/ethyl acetate) to provide tert-butyl 6-methoxy-8-phenylsulfonyl-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (400 mg, 82%) as an off-white solid: 1H NMR (CDCl3, 400 MHz) δ 7.96-7.94 (m, 2H), 7.71 (br s, 1H), 7.58-7.48 (m, 3H), 7.33 (s, 1H), 4.55 (s, 2H), 4.04 (s, 3H), 3.82 (br s, 2H), 2.87 (br s, 2H), 1.50 (s, 9H).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue purified by column chromatography (SiO2, 8:2, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-6bb88c9876654dc89f15d10654be4269
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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