2-(Tributylstannyl)pyridine → HCID 57640429, compound

HRID 388792Notes

Reaction equation

HRID 388792 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][NH:14][C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[O:16])[O:10][N:9]=2)=[CH:4][CH:3]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Sn](CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1>[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][NH:14][C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[O:16])[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 11582095HCID 11582095, compound

Product 1

HCID 57640429HCID 57640429, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Combined the bromide from Example 1 (50 mg, 0.13 mmol) with 2-pyridyltributyl stannane (55 mg, 0.15 mmol) and 5 mL of toluene. The mixture was degassed for three minutes then treated with tetrakistriphenylphosphine palladium (14 mg, 0.013 mmol) and stirred at reflux overnight. The following day the reaction was checked by TLC which showed consumption of the starting bromide and a more polar spot. The reaction was partitioned with aqueous sodium fluoride and ethyl acetate, separated and dried over magnesium sulfate. After filtration and concentration the crude residue was purified by preparative HPLC affording the desired product as a white solid. MS found for C20H16ClN3O2S as (M+H)+ 398.1, 400.1

Workup

  1. customThe mixture was degassed for three minutes
  2. temperatureat reflux overnight
  3. customconsumption of the starting bromide
  4. customThe reaction was partitioned with aqueous sodium fluoride and ethyl acetate
  5. customseparated
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter filtration and concentration the crude residue
  8. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-b73cfbf4f6d843a4816ddc0d795f92f6
Source dataset
uspto-grants-2013_02
Patent number
US08377974B2

Reaction notes

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