Sodium Bicarbonate → HCID 59477820, compound

HRID 1516597Notes

Reaction equation

HRID 1516597 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][O:23]CC4C=CC=CC=4)[CH:17]=3)[C:13]([C:31]#[N:32])=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:1]([O:3][C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][OH:23])[CH:17]=3)[C:13]([C:31]#[N:32])=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 68506464HCID 68506464, compound

Product 1

HCID 59477820HCID 59477820, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Cyano-5-[1-(4-ethoxycarbonylphenyl)-1H-purrole-3-yl]benzoic acid was prepared in a similar manner to that described in Example 10 using 4-[3-cyano-4-(3-benzyloxymethylphenyl)pyrrole-1-yl]benzoic acid ethyl ester. To a solution of the obtained carboxylic acid (1.0 g) in tetrahydrofuran (30 mL) was added boran-tetrahydrofuran complex (1.2 mol/L tetrahydrofuran solution, 3.75 mL) at 0° C., and this mixture was stirred at room temperature for 2 hours. To this reaction mixture was added saturated aqueous sodium bicarbonate solution, and this mixture was extracted with diethyl ether. This organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. This residue was purified by column chromatography on silica gel (eluent: methanol/dichloromethane=1/20) to give the title compound (0.21 g).

Workup

  1. extractionthis mixture was extracted with diethyl ether
  2. washThis organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThis residue was purified by column chromatography on silica gel (eluent: methanol/dichloromethane=1/20)

Sources & evidence

ORD record
ord-111ccf226e60466a8a47f57730b8aac6
Source dataset
uspto-grants-2012_07
Patent number
US08227500B2

Reaction notes

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