Cesium carbonate → HCID 54721818、化合物

HRID 1244088ノート

反応式

HRID 1244088 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([OH:17])=[C:14]([C:18]#[N:19])[C:13](=[O:20])[NH:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.C1(C)C=CC=CC=1.CCO.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[C:16]4[C:15]([OH:17])=[C:14]([C:18]#[N:19])[C:13](=[O:20])[NH:12][C:11]=4[S:10][CH:9]=3)=[CH:4][CH:3]=2)=[CH:24][CH:23]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 2856454-Fluorophenylboronic acidHCID 546964233-(4-Bromophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

生成物 1

HCID 54721818HCID 54721818、化合物

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 21931398DME H2O Toluene EtOH溶媒

反応条件

温度
60 °C

実験手順

To an ambient slurry of 3-(4-bromophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (0.030 g, 0.086 mmol), 4-fluorophenyl boronic acid (0.024 g, 0.173 mmol) and cesium carbonate (0.084 g, 0.26 mmol) in DME/PhCH3/EtOH/H2O (10/1/6/3 ratio, 2 mL) was added palladium tetrakis(triphenylphosphine) (0.001 g, 0.0009 mmol) in a single portion. The reaction was heated at 60° C. for 16 h, cooled to room temperature, filtered, concentrated and purified by RP-HPLC to afford the title compound. MS (DCI/NH3) m/e 362.2 (M+H)+; 1H NMR (300 MHz, DMSO-d6): δ ppm 12.51 (br s, 1H), 7.75 (dd, 2H), 7.64 (d, 2H), 7.52 (d, 2H), 7.31 (apparent t, 2H), 7.07 (s, 1H).

後処理

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompurified by RP-HPLC

出典と根拠

ORDレコード
ord-fbb729ddf842435b9ec60488e065ccd0
出典データセット
uspto-grants-2006_10
特許番号
US07119205B2

反応ノート

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