Stannane, tributyl(1-ethoxyethenyl)- → HCID 53965455, compound

HRID 1780310Notes

Reaction equation

HRID 1780310 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2C(OC(C)(C)C)=O)[CH:5]=[N:6][C:7]=1[Cl:8].[CH2:23]([O:25][C:26]([Sn](CCCC)(CCCC)CCCC)=[CH2:27])[CH3:24].[Sn]>C1(C)C=CC=CC=1.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>[CH2:26]([O:25][C:23]([C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@@H:11]2[CH2:15][CH2:14][CH2:13][NH:12]2)[CH:5]=[N:6][C:7]=1[Cl:8])=[CH2:24])[CH3:27]

Participants

6

Reactant 3

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 5352426Tin atomHCID 22872668HCID 22872668, compound

Product 1

HCID 53965455HCID 53965455, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 5-bromo-6-chloro-3-(1-BOC-2-(S)-pyrrolidinylmethoxy)pyridine (500 mg, 1.28 mmol) in toluene (10.0 mL) was added (1-ethoxyvinyl)tributyltin (489 mL, 1.41 mmol) and tetrakis(triphenylphosphine)palladium(0) (45 mg, 0.-45 mmol). After being refluxed overnight, the resulting mixture was cooled to room temperature. Solvent was removed and the residue was chromatographed on a silica gel column, eluting with hexane/EtOAc 2:1 and 1:1 to afford an oil (568 mg, >100%; some tin reagent contamination). MS (CI/NH3) m/z 383 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.25-1.45 (m, 3H), 1.47 (s, 9H), 1.55-1.71 (m, 1H), 1.98-2.07 (m, 3H), 3.32-3.45 (m, 1H), 3.87-3.96 (m, 2H), 4.05-4.21 (m, 3H), 4.43-4.47 (m, 2H), 7.26-7.34 (m, 1H), 8.03-8.06 (m, 1H).

Workup

  1. temperatureAfter being refluxed overnight
  2. customSolvent was removed
  3. customthe residue was chromatographed on a silica gel column
  4. washeluting with hexane/EtOAc 2:1 and 1:1
  5. customto afford an oil (568 mg, >100%

Sources & evidence

ORD record
ord-e1179d91359f4f49a48c6c3fe2c8747c
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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