Cesium carbonate → 4-Fluoro-1-(2-methoxypyridin-4-yl)-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine

HRID 1662248ノート

反応式

HRID 1662248 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([O:25][CH3:26])[CH: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+]>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].COCCOC.CCO.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]=[CH:23][N:22]=[C:21]([O:25][CH3:26])[CH:20]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:31]2[CH:32]=[N:27][CH:28]=[N:29][CH:30]=2)[CH:3]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 585794981-(3-Bromophenyl)-4-fluoro-1-(2-methoxypyridin-4-yl)-1H-isoindol-3-amine

生成物 1

HCID 462069774-Fluoro-1-(2-methoxypyridin-4-yl)-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine収率 54%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 86587095Dimethoxyethane ethanol water溶媒

反応条件

温度
150 °C

実験手順

1-(3-Bromophenyl)-4-fluoro-1-(2-methoxypyridin-4-yl)-1H-isoindol-3-amine (100 mg, 0.24 mmol), 5-pyrimidinylboronic acid (31.6 mg, 0.25 mmol), [1,1′-bis (diphenylphosphino)ferrocene]palladium(II) chloride (9.90 mg, 0.01 mmol), cesium carbonate (0.058 mL, 0.73 mmol) and DME:EtOH:water (6:3:1) (3.00 mL) were mixed in a microwave vial and heated in a microwave reactor at 150° C. for 20 min. The resulting product mixture was filtered and purified by preparative-HPLC to give 58 mg (54% yield of the title compound (after pooling and freeze drying of the fractions).

後処理

  1. filtrationThe resulting product mixture was filtered
  2. custompurified by preparative-HPLC

出典と根拠

ORDレコード
ord-9e1f968b48c1411d928475e072084f6e
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…