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

HRID 1616883Notes

Reaction equation

HRID 1616883 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[CH2:13][CH2:12][NH:11][C:10]([CH2:15][N:16]4[C:24](=[O:25])[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[C:17]4=[O:26])([CH3:14])[C:9]=3[O:27][C:4]=2[CH:3]=1.CC(C)([O-])C.[Na+].C(O)CO.CN(C)C=O.[F:43][C:44]1[CH:45]=[C:46]([SH:50])[CH:47]=[CH:48][CH:49]=1>[Cu]I>[F:43][C:44]1[CH:45]=[C:46]([S:50][C:2]2[CH:7]=[CH:6][C:5]3[C:8]4[CH2:13][CH2:12][NH:11][C:10]([CH2:15][N:16]5[C:24](=[O:25])[C:23]6[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=6)[C:17]5=[O:26])([CH3:14])[C:9]=4[O:27][C:4]=3[CH:3]=2)[CH:47]=[CH:48][CH:49]=1

Participants

7

Reactant 5

HCID 174Ethylene GlycolHCID 6228DimethylformamideHCID 75710m-FluorobenzenethiolHCID 23676156Sodium t-butoxideHCID 673240232-(7-Iodo-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl)-isoindole-1,3-dione

Product 1

HCID 673238662-[7-(3-Fluoro-phenylsulfanyl)-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl]isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
120 °C

Procedure

To 2-(7-iodo-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl)-isoindole-1,3-dione (0.192 g, 0.406 mmol) was added sodium tert-butoxide (117 mg, 1.22 mmol), copper (I) iodide (7.74 mg, 0.0406 mmol), 1,2-ethanediol (45.3 μL, 0.812 mmol), N,N-dimethylformamide (4.00 mL, 51.6 mmol), and finally 3-fluorobenzenethiol (36.0 μL, 0.427 mmol). The reaction mixture was flushed with N2 and heated at 120° C. under a N2 atmosphere. After 72 h, the reaction was cooled to room temperature and concentrated. The residual solid was partially dissolved into a 5% MeOH in DCM solution and flushed through a plug of Celite. The concentrated filtrate was chromatographed on silica gel using DCM-MeOH—NH4OH to afford a brownish yellow gum. MS m/z 473 [M+H]+.

Workup

  1. customThe reaction mixture was flushed with N2
  2. temperaturethe reaction was cooled to room temperature
  3. concentrationconcentrated
  4. dissolutionThe residual solid was partially dissolved into a 5% MeOH in DCM solution
  5. customflushed through a plug of Celite
  6. customThe concentrated filtrate was chromatographed on silica gel
  7. customto afford a brownish yellow gum

Sources & evidence

ORD record
ord-fc71f21f47bd41a3b98d9aa6ecf04d7c
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

Loading…