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

HRID 2089026노트

반응식

HRID 2089026 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-2d027f35779b451cbfd67127525f9c7d
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08435980B2

반응 노트

불러오는 중…