Methanol → 2-[7-(3-Fluoro-benzenesulfonyl)-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl]isoindole-1,3-dione

HRID 1616884Notes

Reaction equation

HRID 1616884 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:14]=[CH:13][C:12]3[C:15]4[CH2:20][CH2:19][NH:18][C:17]([CH2:22][N:23]5C(=O)[C:30]6[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=6)[C:24]5=[O:33])([CH3:21])[C:16]=4[O:34][C:11]=3[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:35][OH:36].[OH:37]OS([O-])=O.[K+].[OH2:43]>>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:9]2[CH:14]=[CH:13][C:12]3[C:15]4[CH2:20][CH2:19][NH:18][C:17]([CH2:22][N:23]5[C:35](=[O:36])[C:30]6[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=6)[C:24]5=[O:33])([CH3:21])[C:16]=4[O:34][C:11]=3[CH:10]=2)(=[O:37])=[O:43])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 673238662-[7-(3-Fluoro-phenylsulfanyl)-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl]isoindole-1,3-dione

Product 1

HCID 673246722-[7-(3-Fluoro-benzenesulfonyl)-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl]isoindole-1,3-dione

Procedure

To a solution of 2-[7-(3-fluoro-phenylsulfanyl)-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl]isoindole-1,3-dione (0.150 g, 0.317 mmol) in methanol (10.0 mL, 247 mmol) was added a solution of Oxone® (0.488 g, 0.794 mmol) in water (5.0 mL, 280 mmol) and the reaction mixture was stirred at room temperature overnight. After 3 h, the reaction was filtered, concentrated, and extracted with DCM/sat. aq. NaHCO3. The organic layer was dried, concentrated and purified by chromatography to afford 2-[7-(3-fluoro-benzenesulfonyl)-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl]isoindole-1,3-dione as an off-white solid. A suspension of 2-[7-(3-fluoro-benzenesulfonyl)-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl]isoindole-1,3-dione (0.015 g, 0.030 mmol) in ethanol (5.00 mL, 85.6 mmol) was refluxed with hydrazine monohydrate (0.040 mL, 0.80 mmol). After 4 h, the reaction was cooled, filtered, rinsed with MeOH, and the filtrate concentrated and dried under vacuum to afford a yellowish white solid. mp>250° C. dec.; MS m/z 375 [M+H]+. 1H-NMR (400 MHz, CDCl3): δ 1.5 (s, 3H), 2.7 (m, 2H), 3.15 (m, 1H), 3.36 (m, 1H), 4.0 (d, J=14 Hz, 1H), 4.15 (d, J=14 Hz, 1H), 7.2-8.0 (m, 7H)

Workup

  1. waitAfter 3 h
  2. filtrationthe reaction was filtered
  3. concentrationconcentrated
  4. extractionextracted with DCM/
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-3303eec2e5e8421bb641311d138b392a
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

Loading…