Potassium Carbonate → N-(2-Hydroxy-ethyl)-4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yl)-benzenesulfonamide

HRID 1029139

反応式

HRID 1029139 の反応式
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[OH:17][CH2:18][CH2:19][NH:20][S:21]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)(=[O:23])=[O:22].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.O.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[OH:17][CH2:18][CH2:19][NH:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:11]=[CH:10][N:9]=[C:8]3[C:3]=2[C:4]2[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=2[C:6](=[O:12])[NH:7]3)=[CH:26][CH:25]=1)(=[O:23])=[O:22]

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 44119332(4-(N-(2-Hydroxyethyl)sulfamoyl)phenyl)boronic acidHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

生成物 1

HCID 69815493N-(2-Hydroxy-ethyl)-4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yl)-benzenesulfonamide収率 4%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 218864351,4-Dioxane--water (1/1)溶媒HCID 22728543Water ethylacetate溶媒

反応条件

温度
100 °C

実験手順

Compound 83 (100 mg, 0.43 mmol), 4-(2-hydroxyethylsulfamoyl)phenylboronic acid (212 mg, 0.87 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), S-Phos (18 mg, 0.04 mmol), and K2CO3 (299 mg, 2.17 mmol) were dissolved in dioxane/H2O (2.2 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was diluted with H2O/EtOAc, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 0 to 10% MeOH in CH2Cl2. The resulting material was triturated with MeOH, filtered, and dried under vacuum to provide 174 (6 mg, 4% yield) as a light-yellow solid. LC-MS (M+H=396, obsd.=396).

後処理

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with EtOAc
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified via Biotage
  5. washeluting with a gradient of 0 to 10% MeOH in CH2Cl2
  6. customThe resulting material was triturated with MeOH
  7. filtrationfiltered
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-56f590d7ee3541859663f9c58e2073c2
出典データセット
uspto-grants-2014_05
特許番号
US08735584B2

関連ノート

読み込み中…