Dichloromethane → HCID 87192311, 화합물

HRID 2089027노트

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HRID 2089027 반응식
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[C:15]([Cl:17])[N:14]=[C:13]([NH:18][CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)[CH:12]=3)=[CH:9][N:8]([S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:5]2=[N:6][CH:7]=1.[C:34]1([S:40]([N:43]2[CH:47]=[C:46](B3OC(C)(C)C(C)(C)O3)[CH:45]=[N:44]2)(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.ClCCl.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C.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]>[Cl:17][C:15]1[N:14]=[C:13]([NH:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:12]=[C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:46]4[CH:45]=[N:44][N:43]([S:40]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)(=[O:42])=[O:41])[CH:47]=4)[CH:3]=3)[N:8]([S:25]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)(=[O:27])=[O:26])[CH:9]=2)[CH:16]=1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 447552031-(Benzenesulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 866498714-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine

생성물 1

HCID 87192311HCID 87192311, 화합물수율 56.3%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of Example 171a (0.158 g, 0.29 mmol), 1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.100 g, 0.29 mmol), catalytic amount of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane (1:1) and saturated sodium bicarbonate solution (2 mL) in 8 mL dimethylformamide was heated at 65° C. for 2 hours. 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 (20% ethyl acetate/hexane) to afford 0.11 g of the title compound. m/z 673.6 (ESI, M+H)+.

후처리

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel using flash chromatography (20% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-67b794a91b3c4ad4967693a19fa83e61
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08435980B2

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