Ethyl Acetate → 1-(2,6-Dimethylpyrimidin-4-yl)-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine

HRID 1662264노트

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HRID 1662264 반응식
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:19]3[CH:24]=[C:23]([CH3:25])[N:22]=[C:21]([CH3:26])[N:20]=3)[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:18])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[N:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[N:29][CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>COCCOC.CCO.O.[Cl-].[Na+].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].O>[CH3:26][C:21]1[N:20]=[C:19]([C:8]2([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:31]4[CH:32]=[N:27][CH:28]=[N:29][CH:30]=4)[CH:3]=3)[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:18])=[N:9]2)[CH:24]=[C:23]([CH3:25])[N:22]=1

참가 물질

9

반응물 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 585795261-(3-Bromophenyl)-1-(2,6-dimethylpyrimidin-4-yl)-4-fluoro-1H-isoindol-3-amine

생성물 1

HCID 462027441-(2,6-Dimethylpyrimidin-4-yl)-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine수율 16.4%

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 57417360Sodium chloride; water용매HCID 86587095Dimethoxyethane ethanol water용매

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온도
150 °C

실험 절차

1-(3-Bromophenyl)-1-(2,6-dimethylpyrimidin-4-yl)-4-fluoro-1H-isoindol-3-amine (300 mg, 0.73 mmol), pyrimidin-5-ylboronic acid (108 mg, 0.88 mmol), cesium carbonate (713 mg, 2.19 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (59.6 mg, 0.07 mmol) were dissolved in DME:EtOH:water (6:3:1) (5 mL) and heated in a microwave oven for 20 min at 150° C. EtOAc, water and brine were added and the organic phase was collected, dried and filtered. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC to afford 49 mg (15%) of the title compound.

후처리

  1. customthe organic phase was collected
  2. customdried
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-e5bd699261474cb4a7f9849b632f83e1
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030500B2

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