1,4-Dioxane → HCID 66742908, compound

HRID 656341Notes

Reaction equation

HRID 656341 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[F:14].Cl.[NH:16]1[CH2:21][CH2:20][CH2:19][C@H:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17]1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.O1CCOCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:14][C:3]1[CH:4]=[C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][C:2]=1[N:16]1[CH2:21][CH2:20][CH2:19][C@H:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17]1

Participants

7

Reactant 5

HCID 312751,4-DioxaneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 45074034(S)-Ethyl piperidine-3-carboxylate hydrochlorideHCID 666841274-(4-Bromo-3-fluorophenyl)pyridine

Product 1

HCID 66742908HCID 66742908, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A mixture of 4-(4-bromo-3-fluorophenyl)pyridine (190 mg, 0.00075 mol), ethyl (3S)-piperidine-3-carboxylate hydrochloride (180 mg, 0.00090 mol), sodium tert-butoxide (140 mg, 0.0015 mol), palladium acetate (5 mg, 0.00002 mol) and 2-(di-tert-butylphosphino)biphenyl (7 mg, 0.00002 mol) was evacuated and charged with nitrogen and 1,4-dioxane (5 mL, 0.06 mol). The resulting mixture was refluxed overnight. After cooling to ambient temperature, the mixture was filtered and the filtrate was adjusted with TFA to pH=7.0 and purified by CombiFlash (ethyl acetate in hexanes: 60%) to afford the desired product. LCMS: m/z 329.2 (M+H)+.

Workup

  1. customwas evacuated
  2. temperatureThe resulting mixture was refluxed overnight
  3. filtrationthe mixture was filtered
  4. custompurified by CombiFlash (ethyl acetate in hexanes: 60%)

Sources & evidence

ORD record
ord-fe4783c139e942b5907ca49137408f72
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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