Sodium Bicarbonate → HCID 67027249, compound

HRID 446730Notes

Reaction equation

HRID 446730 reaction equation
FC(F)(F)S(O[C:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH:12]=1)(=O)=O.[CH3:22][C:23]1[CH:24]=[C:25](B(O)O)[S:26][CH:27]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.Cl[Pd]Cl.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[CH3:22][C:23]1[CH:24]=[C:25]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][CH2:8]2)[S:26][CH:27]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27343734-Methylthiophene-2-boronic acidHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 67027249HCID 67027249, compound

Reagents, catalysts & solvents 3

HCID 178479797HCID 178479797, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonate (Compound 1061, 2.65 g, 8 mmol, prepared according to the procedure described in Organic Letters, 3(15), pp. 2317-2320, 2001), 4-methylthiophene-2-boronic acid (1.14 g, 8 mmol), and sodium bicarbonate (1.01 g in 10 mL water, 12 mmol) in DMF (30 mL) was degassed with a nitrogen stream for 20 minutes. To the mixture was added tris(diphenylphosphinoferrocene) dichloropalladium (584 mg, 0.8 mmol) and the reaction was stirred for 10 minutes at 120° C. under microwave irradiation. The crude mixture was diluted with ethyl acetate and washed successively with water (2×15 mL) and brine (1×15 mL). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography to afford 1.67 g of tert-butyl 4-(4-methylthiophen-2-yl)piperidine-1-carboxylate (Compound 1062) as a yellow oil; ESMS (M+H)=224.

Workup

  1. washwashed successively with water (2×15 mL) and brine (1×15 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-460b0930c1f74efb85dcc4d52006d7ee
Source dataset
uspto-grants-2013_07
Patent number
US08481524B2

Reaction notes

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