Dichloromethane → 2-[(E)-2-(3,5-dimethoxyphenyl)vinyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 1052242노트

반응식

HRID 1052242 반응식
Br[C:2]1[N:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24](/[CH:30]=[CH:31]/B2OC(C)(C)C(C)(C)O2)[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=1.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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].O>[CH3:29][O:28][C:26]1[CH:25]=[C:24](/[CH:30]=[CH:31]/[C:2]2[N:3]=[C:4]3[CH:10]=[CH:9][N:8]([S:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)(=[O:13])=[O:12])[C:5]3=[N:6][CH:7]=2)[CH:23]=[C:22]([O:21][CH3:20])[CH:27]=1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 162181852-[(1E)-2-(3,5-Dimethoxyphenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 899634192-Bromo-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine

생성물 1

HCID 899631882-[(E)-2-(3,5-dimethoxyphenyl)vinyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine수율 95%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
88 °C

실험 절차

A stirred mixture of 2-bromo-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine (929 mg, 2.75 mmol), 2-[(E)-2-(3,5-dimethoxyphenyl)vinyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (from Aldrich, cat#676160, 838 mg, 2.89 mmol), [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane (1:1) (140 mg, 0.171 mmol), and potassium phosphate (1.20 g, 5.65 mmol) in 1,4-dioxane (20 mL)/water (9.6 mL) was heated at 88° C. After 1 hour, the reaction mixture was quenched with saturated aq. NH4Cl and extracted with methylene chloride. The combined organic layers were dried over MgSO4, filtered, and then concentrated. The residue was purified on silica gel (eluting with 0 to 50% EtOAc in hexanes) to give the desired product (1.10 g, 95%). LCMS calculated for C22H20N3O4S (M+H)+: m/z=422.2. Found: 422.2.

후처리

  1. customthe reaction mixture was quenched with saturated aq. NH4Cl
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (eluting with 0 to 50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-64b5732f4f374fa8a9f4ed4dcc5735e3
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388185B2

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