Tributylvinyltin → HCID 68086035, compound

HRID 514006Notes

Reaction equation

HRID 514006 reaction equation
FC(F)(F)S(O[C:7]1[C:16]([CH3:17])=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:18]1[C:27]2[C:22]3=[C:23]([CH2:28][CH2:29][O:30][C:21]3=[CH:20][CH:19]=1)[CH:24]=[CH:25][N:26]=2)(=O)=O.[CH2:33]([Sn](CCCC)(CCCC)C=C)[CH2:34]CC.[Li+].[Cl-]>O1CCOCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:17][C:16]1[C:7]([CH:33]=[CH2:34])=[C:8]([C:18]2[C:27]3[C:22]4=[C:23]([CH2:28][CH2:29][O:30][C:21]4=[CH:20][CH:19]=2)[CH:24]=[CH:25][N:26]=3)[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

7

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 86691532HCID 86691532, compound

Product 1

HCID 68086035HCID 68086035, compoundYield 113%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-3-methylnaphthalen-2-yltrifluoromethanesulfonate (5E) (89 mg, 0.194 mmol), tributyl(vinyl)tin (0.23 mL, 0/776 mmol), Pd(PPh3)4 (34 mg, 0.029 mmol) and LiCl (16 mg, 0.39 mmol) in dioxane (3 mL) was stirred at 110° C. under Ar for 5 hours. The reaction mixture was cooled, diluted with ethyl acetate and washed with saturated NaHCO3 solution (2×), brine and dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, hexanes) to give 5F as a white solid (74 mg, 91%). LCMS-ESI+ (m/z): [M+H]+ calcd for C24H20NO: 338.42. Found: 338.2.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with saturated NaHCO3 solution (2×), brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (silica gel, hexanes)

Sources & evidence

ORD record
ord-3f6b6227d2924987ab26e85a46e8bc38
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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