Sodium Bicarbonate → HCID 818845, compound

HRID 1611603Notes

Reaction equation

HRID 1611603 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8].[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O)([O-:11])=[O:10].C([O-])(O)=O.[Na+]>COCCOC.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>[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8])([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2773548(2-Nitrophenyl)boronic acidHCID 27970793-Bromothiophene-2-carboxaldehyde

Product 1

HCID 818845HCID 818845, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The compound 3-bromothiophen-2-aldehyde (2) (5.20 g, 27 mmol), solubilized in ethylene glycol dimethyl ether (105 ml) was treated with (Ph3P)4Pd (936 mg, 0.81 mmol), with 2-nitrophenylboronic acid (5 g, 30 mmol) and an aqueous solution of 2M NaHCO3 (70 ml). The reaction mixture was then refluxed for 5 hrs. Then the mixture was cooled to room temperature, the solvent was partially removed under reduced pressure and the resulting mixture was extracted with ethyl acetate (4×100 ml). The combined organic layer was washed with a saturated solution of NaCl, dried (Na2SO4), and evaporated under reduced pressure. The mixture was chromatographed using 80/20 petroleum ether/ethyl acetate, thus giving the derivative (8) (4.5 g, 83% yield).

Workup

  1. temperatureThe reaction mixture was then refluxed for 5 hrs
  2. customthe solvent was partially removed under reduced pressure
  3. extractionthe resulting mixture was extracted with ethyl acetate (4×100 ml)
  4. washThe combined organic layer was washed with a saturated solution of NaCl
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe mixture was chromatographed

Sources & evidence

ORD record
ord-672817bdbe06462a9d963a255a4bca7c
Source dataset
uspto-grants-2006_01
Patent number
US06989388B2

Reaction notes

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