Dichloromethane → HCID 89996187, 화합물

HRID 1480819노트

반응식

HRID 1480819 반응식
[CH3:1][O:2][C:3]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[CH:6][C:4]=1[NH2:5].I[C:20]1[CH:21]=[N:22][N:23]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[CH:24]=1.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:28][N:27]([CH3:29])[CH2:26][CH2:25][N:23]1[CH:24]=[C:20]([C:8]2[CH:7]=[CH:6][C:4]([NH2:5])=[C:3]([O:2][CH3:1])[CH:9]=2)[CH:21]=[N:22]1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 177502072-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 644311982-(4-Iodo-1H-pyrazol-1-yl)-N,N-dimethylethanamine

생성물 1

HCID 89996187HCID 89996187, 화합물수율 28%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (313 mg, 1.256 mmol), 2-(4-iodo-1H-pyrazol-1-yl)-N,N-dimethylethanamine (Preparation 62, 270 mg, 1.019 mmol) and Pd(dppf)Cl2.DCM (80 mg, 0.098 mmol) was dissolved in THF (4.5 mL) and 2M sodium carbonate in water (1.5 mL) and heated to 60° C. for 18 hours. The mixture was concentrated under reduced pressure. The residue was partitioned between water and DCM and the aqueous layer extracted with DCM three times. The combined organic layers were dried and concentrated. The residue was purified by silica gel column chromatography eluting with 0 to 10% MeOH in DCM to give the title compound (74 mg, 28%).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was partitioned between water and DCM
  3. extractionthe aqueous layer extracted with DCM three times
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 0 to 10% MeOH in DCM

출처 및 근거

ORD 기록
ord-04864b512dd54374a5b06bee5fa981f3
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409907B2

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