Dichloromethane → 4-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine

HRID 2089026ノート

反応式

HRID 2089026 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.Cl[CH2:22][Cl:23].C(=O)(O)[O-].[Na+].C(O[CH2:33][CH3:34])(=O)C>CN(C)C=O.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:3]3[CH:2]=[C:22]([Cl:23])[N:6]=[C:5]([NH:8][CH:34]4[CH2:33][CH2:17][CH2:16][CH2:15][CH2:20]4)[CH:4]=3)=[CH:9][N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 242292401-Benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 866498714-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 5-bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.155 g, 2.49 mmol), Example 168a (0.924 g, 2.74 mmol), catalytic amount of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane (1:1) and saturated sodium bicarbonate solution (6 mL) in 24 mL dimethylformamide was heated at 65° C. for 30 minutes. The material was cooled to room temperature, diluted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified on silica gel using flash chromatography (6% ethyl acetate/hexane) to afford 0.68 g of the title compound. m/z 547.4 (APCI, M+H)+.

後処理

  1. customwas heated at 65° C. for 30 minutes
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel using flash chromatography (6% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-2d027f35779b451cbfd67127525f9c7d
出典データセット
uspto-grants-2013_05
特許番号
US08435980B2

反応ノート

読み込み中…