Sodium Carbonate → HCID 67257290, compound

HRID 2371040Notes

Reaction equation

HRID 2371040 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]1([OH:19])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]1.[OH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:19][C:7]1([C:6]2[CH:5]=[CH:4][S:3][C:2]=2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[OH:20])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2773454(2-Hydroxyphenyl)boronic acidHCID 67257288HCID 67257288, compound

Product 1

HCID 67257290HCID 67257290, compoundYield 88.2%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl 3-(2-bromothiophen-3-yl)-3-hydroxypyrrolidine-1-carboxylate (5 g, 13.8 mmol), Pd(OAc)2 (31 mg, 0.14 mmol), Ph3P (147 mg, 0.42 mmol), 2-hydroxyphenylboronic acid (1.74 g, 27.6 mmol) and Na2CO3 (2.9 g, 27.6 mmol) in dioxane (10 mL) and water (10 mL) was refluxed under N2 for 3 h. After the reaction was cooled to room temperature, the reaction mixture was extracted with EtOAc several times. The combined organic layers were washed with brine, and dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (4.4 g, 88%).

Workup

  1. temperaturewas refluxed under N2 for 3 h
  2. extractionthe reaction mixture was extracted with EtOAc several times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-c975866b216f4ea9beda56d1e6fc914f
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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