Pyruvic Acid → 5-cyano-1H-indole-2-carboxylic Acid

HRID 1512735ノート

反応式

HRID 1512735 の反応式
[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]

参加物

6

反応物 3

HCID 1060Pyruvic AcidHCID 9237DabcoHCID 44163954-Amino-3-iodobenzonitrile

生成物 1

HCID 71446255-cyano-1H-indole-2-carboxylic Acid収率 59.1%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
105 °C

実験手順

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.

後処理

  1. customThe solvent was evaporated
  2. additionEtOAc (200 mL) was added
  3. washthe resulting solution was washed with water (100 mL) and aqueous NaOH solution (20 mL)
  4. extractionThe combined aqueous solution was extracted with EtOAc (3×150 mL)
  5. dry with materialThe combined solution was dried over anhydrous magnesium sulfate
  6. concentrationThe dried solution was concentrated
  7. customThe residue was triturated

出典と根拠

ORDレコード
ord-53b2dbee50f043c9a45d4c73180e59cc
出典データセット
uspto-grants-2012_07
特許番号
US08217028B2

反応ノート

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