Sodium Carbonate → HCID 58442820, compound

HRID 41645Notes

Reaction equation

HRID 41645 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9](Br)=[CH:8][S:7][CH:6]=1)=[O:4].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH:20]=[C:21]([C:9]2[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][S:7][CH:8]=2)[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 13487917Methyl 4-bromothiophene-3-carboxylate

Product 1

HCID 58442820HCID 58442820, compoundYield 53.8%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-bromothiophene-3-carboxylic acid methyl ester (500 mg, 2.3 mmol, 1.0 eq.) in THF (40 mL) was combined with 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (0.7 g, 2.3 mmol, 1 eq.) under nitrogen. A solution of Na2CO3 (960 mg) in water (4.5 mL) was added, followed by the addition of PdCl2(PPh3)2 (80 mg, 0.1 mmol, 0.4 eq.). The resulting solution was stirred for 18 hours while the temperature was maintained at reflux in an oil bath. The resulting solution was diluted with EtOAc (50 mL), then washed with saturated aqueous NaCl (2×100 mL). The organic layer was concentrated and the residue was applied onto a silica gel column and eluted with EtOAc/PE (1:30) to yield 4-(4-methoxycarbonylthiophen-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (0.4 g) as a light yellow oil.

Workup

  1. temperaturewas maintained
  2. temperatureat reflux in an oil bath
  3. washwashed with saturated aqueous NaCl (2×100 mL)
  4. concentrationThe organic layer was concentrated
  5. washeluted with EtOAc/PE (1:30)

Sources & evidence

ORD record
ord-f9ed7bb33da34988a7a1f527f2570750
Source dataset
uspto-grants-2013_09
Patent number
US08530663B2

Reaction notes

Loading…