Pyruvic Acid → 5-cyano-1H-indole-2-carboxylic Acid
Reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1I.O=[C:12]([CH3:16])[C:13]([OH:15])=[O:14].C1N2CCN(CC2)C1>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:6]([C:5]1[CH:4]=[C:3]2[C:2](=[CH:9][CH:8]=1)[NH:1][C:12]([C:13]([OH:15])=[O:14])=[CH:16]2)#[N:7]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 105 °C
Procedure
A suspension of 4-amino-3-iodobenzonitrile (2.44 g), 2-oxopropanoic acid (2.64 g), DABCO (3.36 g), and Pd(OAc)2 in DMF (30 mL) was heated to 105° C. and stirred at that temperature for 1 hour. The solvent was evaporated. EtOAc (200 mL) was added and the resulting solution was washed with water (100 mL) and aqueous NaOH solution (20 mL). The combined aqueous solution was extracted with EtOAc (3×150 mL). The organic fractions were combined. The combined solution was dried over anhydrous magnesium sulfate. The dried solution was concentrated. The residue was triturated to afford 5-cyano-1H-indole-2-carboxylic acid (D20) (1.1 g) as a brown solid.
Workup
- customThe solvent was evaporated
- additionEtOAc (200 mL) was added
- washthe resulting solution was washed with water (100 mL) and aqueous NaOH solution (20 mL)
- extractionThe combined aqueous solution was extracted with EtOAc (3×150 mL)
- dry with materialThe combined solution was dried over anhydrous magnesium sulfate
- concentrationThe dried solution was concentrated
- customThe residue was triturated
Sources & evidence
- ORD record
- ord-53b2dbee50f043c9a45d4c73180e59cc
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08217028B2
Reaction notes
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