Benzothiazole → HCID 53757231, compound

HRID 1837938Notes

Reaction equation

HRID 1837938 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C([Li])CCC.[C:15]([O:19][C:20](=[O:47])[CH:21]=[C:22](OS(C(F)(F)F)(=O)=O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[CH:38]=[CH:37][C:36]2[CH2:35][CH2:34][CH2:33][NH:32][C:31]=2[N:30]=1)([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])O.[Na+]>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[C:15]([O:19][C:20](=[O:47])[CH:21]=[C:22]([C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[CH:38]=[CH:37][C:36]2[CH2:35][CH2:34][CH2:33][NH:32][C:31]=2[N:30]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 7222BenzothiazoleHCID 516892Sodium BicarbonateHCID 54554919HCID 54554919, compoundHCID 178418339Butyllithium

Product 1

HCID 53757231HCID 53757231, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of benzthiazole (165 mg, 1.22 mmol) in anhydrous tetrahydrofuran (5 mL) at −78° C. was added a solution of n-butyllithium in hexanes (0.52 mL of a 2.5 M solution). After 5 minutes, a solution of zinc chloride in tetrahydrofuran (2.6 mL of a 0.50 M solution) was added and the reaction mixture was allowed to warm to ambient temperature. To the resulting solution was added 9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-3-(trifluoromethanesulfonyloxy)-non-2-enoic acid tert-butyl ester 29-6 (400 mg, 0.81 mmol) and palladium(tetrakis)-triphenylphosphine (94 mg, 0.081 mmol) and the mixture was stirred at ambient temperature for 1 hour. The reaction mixture was then poured into saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried with anhydrous magnesium sulfate, filtered, and concentrated at reduced pressure. The resulting oil was purified by flash column chromatography over silica gel with 4:1 ethyl acetate/hexanes to give 29-7c as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure
  6. customThe resulting oil was purified by flash column chromatography over silica gel with 4:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-73d5c3c2debe4b94998f1f4b36949b5f
Source dataset
uspto-grants-2004_08
Patent number
US06784190B2

Reaction notes

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