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

HRID 1512735노트

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HRID 1512735 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 71446255-cyano-1H-indole-2-carboxylic Acid수율 59.1%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

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온도
105 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-53b2dbee50f043c9a45d4c73180e59cc
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217028B2

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