Dimethylformamide → ethyl 4,6-dicyano-1H-indole-2-carboxylate

HRID 62648

반응식

HRID 62648 반응식
Cl[C:2]1[CH:10]=[C:9](Cl)[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:6]2.[C:17]([Zn]C#N)#[N:18].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[CH3:56][N:57](C=O)C>O.N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:17]([C:2]1[CH:10]=[C:9]([C:56]#[N:57])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:6]2)#[N:18]

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 2736407ethyl 4,6-dichloro-1H-indole-2-carboxylateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 178514179HCID 178514179, 화합물

생성물 1

HCID 89995321ethyl 4,6-dicyano-1H-indole-2-carboxylate수율 32%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 222Ammonia용매HCID 962Water용매

반응 조건

온도
160 °C

실험 절차

To an argon purged solution of ethyl 4,6-dichloro-1H-indole-2-carboxylate (I-1c: 1 g, 3.89 mmol) in DMF (8 mL) were added dicyanozinc (1.37 g, 11.67 mmol), Pd2(dba)3 (356 mg, 0.389 mmol) followed by Xphos (166 mg. 0.389 mmol), the mixture was then stirred in microwave at 160° C. for 14 h. The resultant reaction mixture was allowed to cool to room temperature, diluted with water (10 mL) and ammonia solution (2 mL; Specific Gravity 0.91). The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with water, brine, dried over anhydrous Na2SO4 solution and concentrated. The crude compound was purified by column chromatography over silica gel (100-200 mesh) using a solvent gradient of 6% ethyl acetate in chloroform as eluent to afford 300 mg (32%) of ethyl 4,6-dicyano-1H-indole-2-carboxylate (I-2a) as a brown solid.

후처리

  1. customThe resultant reaction mixture
  2. temperatureto cool to room temperature
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4 solution
  6. concentrationconcentrated
  7. customThe crude compound was purified by column chromatography over silica gel (100-200 mesh)

출처 및 근거

ORD 기록
ord-41af761c9581408a806f6f2bca9ca8bd
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447039B2

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