Sodium Bicarbonate → HCID 67175633, compound

HRID 1188286Notes

Reaction equation

HRID 1188286 reaction equation
Br[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:8]=2[CH3:15])[C:5]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:4][CH:3]=1.C1[C:29]2[CH:28]=[CH:27][C:26]([O:30]B(OO)OO)=[CH:25][C:24]1=2.[C:36](=O)(O)[O-:37].[Na+]>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>[O:30]1[C:26]2[CH:27]=[CH:28][C:29]([C:2]3[N:6]([C:7]4[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:8]=4[CH3:15])[C:5]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:4][CH:3]=3)=[CH:24][C:25]=2[O:37][CH2:36]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 58305685HCID 58305685, compoundHCID 131731246HCID 131731246, compound

Product 1

HCID 67175633HCID 67175633, compoundYield 115.1%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a suspension of ethyl 3-(5-bromo-1-(4-cyano-2-methylphenyl)-1H-pyrrol-2-yl)propanoate (400 mg, 0.665 mmol), 3,4-methylenedioxylphenylboric acid (143 mg, 0.864 mmol), sodium bicarbonate (560 mg, 5.32 mmol) in solvent (4 mL) was added Pd(PPh3)4 (60 mg, 0.199 mmol). The reaction was degassed and heated to reflux for 5 h. TLC showed that the reaction was completed. Water (4 mL) was added and the mixture was extracted with ethyl acetate (5 mL×3). The combined organic layers were dried with magnesium sulfate, filtered and evaporated to obtain a brown oil, which was purified by silica gel column chromatography to afford ethyl 3-(5-(benzo[d][1,3]dioxol-5-yl)-1-(4-cyano-2-methylphenyl)-1H-pyrrol-2-yl)propanoate as a colorless oil (308 mg, 69%).

Workup

  1. customThe reaction was degassed
  2. temperatureheated
  3. temperatureto reflux for 5 h
  4. additionWater (4 mL) was added
  5. extractionthe mixture was extracted with ethyl acetate (5 mL×3)
  6. dry with materialThe combined organic layers were dried with magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto obtain a brown oil, which
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-414b0886d92745e586761e49c7b6f4ab
Source dataset
uspto-grants-2014_03
Patent number
US08673961B2

Reaction notes

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