Sodium Bicarbonate → HCID 18470730, compound

HRID 2228627Notes

Reaction equation

HRID 2228627 reaction equation
Br[C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:4]([C:13]([O:15][CH3:16])=[O:14])[C:3]=1[CH3:17].[N:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>C(COC)OC.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>[CH3:17][C:3]1[C:4]([C:13]([O:15][CH3:16])=[O:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:6][C:2]=1[C:21]1[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 18470737HCID 18470737, compound

Product 1

HCID 18470730HCID 18470730, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of methyl 5-bromo-4-methyl-2-phenylpyrrole-3-carboxylate (82 mg, 0.278 mmol), 4-pyridylboronic acid (68 mg, 0.556 mmol), PdCl2(PPh3)2 (20 mg, 0.0278 mmol), and saturated aqueous NaHCO3 (0.3 mL) in dimethoxyethane (1.5 mL) was refluxed for 16 hours. The mixture was extracted with CH2Cl2 (10 mL×3), the combined organic layer dried over Na2SO4, and concentrated ini vacito. The residue was purified by PTLC (1 mm) with acetone-hexane (1:2) to afford the title compound (37 mg, 46% yield).

Workup

  1. temperaturewas refluxed for 16 hours
  2. extractionThe mixture was extracted with CH2Cl2 (10 mL×3)
  3. dry with materialthe combined organic layer dried over Na2SO4
  4. concentrationconcentrated ini vacito
  5. customThe residue was purified by PTLC (1 mm) with acetone-hexane (1:2)

Sources & evidence

ORD record
ord-19ae69f1efa84099ad546a69a9eabeba
Source dataset
uspto-grants-2002_07
Patent number
US06417202B1

Reaction notes

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