Sodium Carbonate → HCID 118046190, 화합물

HRID 596066노트

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HRID 596066 반응식
[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][N:3]=1.F[CH:29](F)[N:30]1[CH:34]=[C:33](I)[C:32](C)=[N:31]1.C([O-])([O-])=O.[Na+].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>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].CCOC(C)=O.COCCOC>[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5]([C:33]2[CH:32]=[N:31][N:30]([CH3:29])[CH:34]=2)=[CH:4][N:3]=1

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 463183071-(Difluoromethyl)-4-iodo-3-methyl-1H-pyrazoleHCID 123330616HCID 123330616, 화합물

생성물 1

HCID 118046190HCID 118046190, 화합물

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A mixture of crude methyl 4-(2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-2-fluorobenzoate (712 mg, 1.912 mmol), 1-(difluoromethyl)-4-iodo-3-methyl-1H-pyrazole (740 mg, 2.87 mmol), PdCl2(dppf) (70.0 mg, 0.096 mmol), DME (7.899 mL), and 2M Na2CO3 (3.95 mL) was heated at 100° C. overnight. After adding Na2SO4 followed by dilution with EtOAc, the reaction mixture was filtered off and the resulting volatile materials were concentrated in vacuo. The crude product was purified by flash chromatography eluting with 0-100% of EtOAc in DCM. LCMS (m/z): 491.1 (MH+), 0.64 min

후처리

  1. filtrationthe reaction mixture was filtered off
  2. concentrationthe resulting volatile materials were concentrated in vacuo
  3. customThe crude product was purified by flash chromatography
  4. washeluting with 0-100% of EtOAc in DCM
  5. custom491.1 (MH+), 0.64 min

출처 및 근거

ORD 기록
ord-82a1d98e52b84479b39aa76c01f42891
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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