Cesium carbonate → HCID 54721818, 화합물

HRID 1244088노트

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HRID 1244088 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 54721818HCID 54721818, 화합물

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 21931398DME H2O Toluene EtOH용매

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온도
60 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-fbb729ddf842435b9ec60488e065ccd0
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119205B2

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