Tributylvinyltin → HCID 68109354, compound

HRID 2179389Notes

Reaction equation

HRID 2179389 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12](OS(C(F)(F)F)(=O)=O)[C:13]3[O:22][C:21]4[CH2:20][CH2:19][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:17][C:16]=4[C:14]=3[CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:38]([Sn](CCCC)(CCCC)C=C)[CH2:39]CC.[Cl-].[Li+]>O1CCOCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]([CH:38]=[CH2:39])[C:13]3[O:22][C:21]4[CH2:20][CH2:19][N:18]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:17][C:16]=4[C:14]=3[CH:15]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 86668002HCID 86668002, compound

Product 1

HCID 68109354HCID 68109354, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl 8-(phenylsulfonyl)-6-(((trifluoromethyl)sulfonyl)oxy)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (200 mg, 0.45 mmol), tributyl(vinyl)stannane (0.11 mL, 0.48 mmol), lithium chloride (45 mg, 1.34 mmol) and palladium tetrakis(triphenylphosphine) (8 mg, 0.01 mmol) was suspended in anhydrous 1,4-dioxane (5 mL). The flask was purged with argon, sealed, and heated to 100° C. for 3 h. The reaction mixture was cooled to ambient temperature, diluted with water, and extracted with ethyl acetate. The organic extract was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate) to give tert-butyl 8-(phenylsulfonyl)-6-vinyl-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (120 mg, 77%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.00-7.90 (m, 3H), 7.86 (s, 1H), 7.61-7.45 (m, 3H), 7.00-6.84 (m, 1H), 6.23 (d, J=17.4 Hz, 1H), 5.60 (d, J=17.4 Hz, 1H), 4.57 (s, 2H), 3.84 (t, J=5.7 Hz, 2H), 2.88 (br s, 2H), 1.51 (s, 9H).

Workup

  1. customThe flask was purged with argon
  2. customsealed
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. extractionThe organic extract
  7. dry with materialwas dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-6a355909029744df884293aec2cab5fc
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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