3-(Tributylstannyl)pyridine → HCID 89618184, compound

HRID 1502576Notes

Reaction equation

HRID 1502576 reaction equation
Br[C:2]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:3]=1[CH2:4][CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]12.C([Sn](CCCC)(CCCC)[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)CCC>C1(C)C=CC=CC=1.[Pd].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>[O:10]=[C:8]1[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]2[C:18]3[C:3]([CH2:4][CH:5]2[CH2:9]1)=[C:2]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)[CH:21]=[CH:20][CH:19]=3

Participants

5

Reactant 2

HCID 34838483-(Tributylstannyl)pyridineHCID 67989352HCID 67989352, compound

Product 1

HCID 89618184HCID 89618184, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Tert-butyl 5-bromo-2-oxo-3,3a,4,8b-tetrahydroindeno[1,2-b]pyrrole-1-carboxylate (Example 1. Step 3, 0.500 g, 1.42 mmol), tributyl(3-pyridyl)stannane (0.784 g, 2.12 mmol) and tetrakis(triphenylphosphine) palladium (0.164 g, 0.142 mmol) were dissolved in toluene. The mixture was irradiated in the microwave at 160° C. and normal absorption level for 5 minutes. The toluene was removed and the mixture was taken up in acetonitrile and n-hexan. The hexane layer was extracted again with acetonitrile and the combined acetonitrile layers were dried over sodium sulphate and evaporated. The crude was purified by flash chromatography to give tert-butyl 2-oxo-5-(3-pyridyl)-3,3a,4,8b-tetrahydroindeno[1,2-b]pyrrole-1-carboxylate E11 (0.409 g, 82%); LCMS (method A) RT 1.45 min; ES+351 (M+H+). The compounds E9-E13 were prepared according to this procedure.

Workup

  1. customThe mixture was irradiated in the microwave at 160° C.
  2. customThe toluene was removed
  3. extractionThe hexane layer was extracted again with acetonitrile
  4. dry with materialthe combined acetonitrile layers were dried over sodium sulphate
  5. customevaporated
  6. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-58fba8fb6f43497891c217978c3e2a84
Source dataset
uspto-grants-2015_12
Patent number
US09210929B2

Reaction notes

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