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

HRID 62648

反応式

HRID 62648 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 222Ammonia溶媒HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-41af761c9581408a806f6f2bca9ca8bd
出典データセット
uspto-grants-2016_09
特許番号
US09447039B2

関連ノート

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