Dimethylformamide → HCID 67323579, compound

HRID 1616881Notes

Reaction equation

HRID 1616881 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][NH:16][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])([CH3:14])[C:9]=3[O:22][C:4]=2[CH:3]=1.CC1C=CC2C=CC3C=CC(C)=NC=3C=2N=1.CN(C)C=O.[F:44][C:45]1[CH:46]=[C:47]([SH:51])[CH:48]=[CH:49][CH:50]=1.CC(C)([O-])C.[Na+]>[Cu]I>[F:44][C:45]1[CH:46]=[C:47]([S:51][C:2]2[CH:7]=[CH:6][C:5]3[C:8]4[CH2:13][CH2:12][NH:11][C:10]([CH2:15][NH:16][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])([CH3:14])[C:9]=4[O:22][C:4]=3[CH:3]=2)[CH:48]=[CH:49][CH:50]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 652372,9-Dimethyl-1,10-phenanthrolineHCID 75710m-FluorobenzenethiolHCID 23676156Sodium t-butoxideHCID 67323146HCID 67323146, compound

Product 1

HCID 67323579HCID 67323579, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
100 °C

Procedure

To N-(7-iodo-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl)-isobutyramide (230 mg, 0.56 mmol), neocuproine (11.6 mg, 0.0558 mmol) and copper (I) iodide (53.1 mg, 0.279 mmol) was added dry N,N-dimethylformamide (4 mL, 50 mmol). 3-Fluorobenzenethiol (104 μL, 1.23 mmol) was added neat followed immediately by the addition of the sodium tert-butoxide (118 mg, 1.23 mmol). The reaction mixture was stirred at 100° C. After 48 h, the reaction mixture was cooled to room temperature and concentrated. The residual solid was partially dissolved into a 5% MeOH in DCE solution and flushed through a plug of Celite. The concentrated filtrate was chromatographed with DCM-MeOH—NH4OH to afford a brownish yellow gum. MS m/z 413 [M+H]+.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. dissolutionThe residual solid was partially dissolved into a 5% MeOH in DCE solution
  4. customflushed through a plug of Celite
  5. customThe concentrated filtrate was chromatographed with DCM-MeOH—NH4OH
  6. customto afford a brownish yellow gum

Sources & evidence

ORD record
ord-e55870f9c6d04918b2e909976e80c775
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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