Ethyl Acetate → 4-Fluoro-1-(5-methoxy-4,6-dimethylpyridin-2-yl)-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine

HRID 1662263ノート

反応式

HRID 1662263 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:19]3[CH:24]=[C:23]([CH3:25])[C:22]([O:26][CH3:27])=[C:21]([CH3:28])[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:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[N:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>COCCOC.CCO.O.[Cl-].[Na+].O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].O>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[C:10]([NH2:18])=[N:9][C:8]2([C:19]1[CH:24]=[C:23]([CH3:25])[C:22]([O:26][CH3:27])=[C:21]([CH3:28])[N:20]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:33]2[CH:34]=[N:29][CH:30]=[N:31][CH:32]=2)[CH:3]=1

参加物

9

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 585795341-(3-Bromophenyl)-4-fluoro-1-(5-methoxy-4,6-dimethylpyridin-2-yl)-1H-isoindol-3-amine

生成物 1

HCID 462027434-Fluoro-1-(5-methoxy-4,6-dimethylpyridin-2-yl)-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine収率 17%

試薬・触媒・溶媒 4

HCID 53485975CID 53485975触媒HCID 962Water溶媒HCID 57417360Sodium chloride; water溶媒HCID 86587095Dimethoxyethane ethanol water溶媒

実験手順

1-(3-Bromophenyl)-4-fluoro-1-(5-methoxy-4,6-dimethylpyridin-2-yl)-1H-isoindol-3-amine (272 mg, 0.62 mmol), pyrimidin-5-ylboronic acid (92 mg, 0.74 mmol), cesium carbonate (604 mg, 1.85 mmol) and dichloro[1,1′-bis (diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (50.4 mg, 0.06 mmol) were dissolved in DME:EtOH:water (6:3:1) (5 mL) and irradiated in a microwave oven for 20 min at 150° C. EtOAc, water and brine were added and the organic phase was collected, dried (Na2SO4) and filtered. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC to afford 45 mg (17%) of the title compound.

後処理

  1. customirradiated in a microwave oven for 20 min at 150° C
  2. customthe organic phase was collected
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-0d0c4774c20a4a5db87b6a5563a1ff12
出典データセット
uspto-grants-2011_10
特許番号
US08030500B2

反応ノート

読み込み中…