Ethylene Glycol → HCID 67324889, compound

HRID 1616866Notes

Reaction equation

HRID 1616866 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:10]([CH3:22])([CH3:21])[C:9]=3[O:23][C:4]=2[CH:3]=1.CC(C)([O-])C.[Na+].C(O)CO.CN(C)C=O.[F:39][C:40]1[CH:41]=[C:42]([SH:46])[CH:43]=[CH:44][CH:45]=1>[Cu]I>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][C:8]2[C:5]3[CH:6]=[CH:7][C:2]([S:46][C:42]4[CH:43]=[CH:44][CH:45]=[C:40]([F:39])[CH:41]=4)=[CH:3][C:4]=3[O:23][C:9]=2[C:10]1([CH3:22])[CH3:21])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 5

HCID 174Ethylene GlycolHCID 6228DimethylformamideHCID 75710m-FluorobenzenethiolHCID 23676156Sodium t-butoxideHCID 67324040HCID 67324040, compound

Product 1

HCID 67324889HCID 67324889, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
120 °C

Procedure

To tert-butyl 7-iodo-1,1-dimethyl-3,4-dihydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate P30 (0.505 g, 1.18 mmol) was added sodium tert-butoxide (341 mg, 3.55 mmol), copper(I) iodide (20 mg, 0.08 mmol), 1,2-ethanediol (132 μL, 2.38 mmol), N,N-dimethylformamide (17 mL, 210 mmol), and finally 3-Fluoro-benzenethiol (101 μL, 1.19 mmol). The reaction mixture was flushed with N2 and heated at 120° C. under N2. After 15 h, the reaction mixture was concentrated under high vacuum, the residue dissolved in 5% methanol-methylene chloride and then filtered through a celite-silica plug. The filtrate was concentrated and purified by silica chromatography (EtOAc/hexane) to afford the product as a pale yellow oil. MS m/z: 428 [M+H]+.

Workup

  1. customThe reaction mixture was flushed with N2
  2. concentrationthe reaction mixture was concentrated under high vacuum
  3. dissolutionthe residue dissolved in 5% methanol-methylene chloride
  4. filtrationfiltered through a celite-silica plug
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-5e983adcc6684dbc9df917dc8068f941
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

Loading…