Dimethylformamide → HCID 69219560, compound

HRID 272722Notes

Reaction equation

HRID 272722 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([O:24][CH3:25])=[CH:9][C:10]2[NH:16][C:15]3[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:14]=3[C:13](=[O:22])[NH:12][C:11]=2[CH:23]=1)(=O)=O.[CH2:28]([Sn](CCCC)(CCCC)C=C)[CH2:29]CC.[Li+].[Cl-].CN(C=O)C>[F-].[K+].C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:21][C:18]1[CH:19]=[CH:20][C:14]2[C:13](=[O:22])[NH:12][C:11]3[CH:23]=[C:7]([CH:28]=[CH2:29])[C:8]([O:24][CH3:25])=[CH:9][C:10]=3[NH:16][C:15]=2[CH:17]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 87737486HCID 87737486, compound

Product 1

HCID 69219560HCID 69219560, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 522689Potassium FluorideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of Example 515B (210 mg, 0.5 mmol), tributyl(vinyl)tin (175 μL, 0.6 mmol), Pd(PPh3)2Cl2 (35 mg, 0.05 mmol), LiCl (169 mg, 4.0 mmol) and DMF was flushed with nitrogen, heated at 50° C. overnight, cooled to room temperature, diluted with a saturated potassium fluoride solution, stirred 15 minutes, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by column chromatography on silica gel with a solvent gradient of 4:1 to 1:1 hexane/ethyl acetate to give 77 mg (52%) of the desired product. MS (ESI) m/e 301 (M+H)+; 1H NMR (300 MHz, DMSO-d6) □ 9.72 (s, 1H), 8.14 (s, 1H), 7.68 (d, J=8.5 Hz, 1H), 7.11 (s, 1H), 7.05 (d, J=2.0 Hz, 1H), 6.94 (dd, J=2.0, 8.5 Hz, 1H), 6.80 (dd, J=11.2, 18.0 Hz, 1H), 6.63 (s, 1H), 5.56 (dd, J=1.5, 17.8 Hz, 1H), 5.14 (dd, J=1.7, 11.2 Hz, 1H), 3.75 (s, 3H).

Workup

  1. temperaturecooled to room temperature
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography on silica gel with a solvent gradient of 4:1 to 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-c88adc2438ea4e7fb389e31da69758b8
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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