Sodium Carbonate → 12-[1-(oxan-2-yl)-1H-pyrazol-5-yl]-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene

HRID 1530557ノート

反応式

HRID 1530557 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:16]3[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:18][N:17]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2.[O:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[N:30]1[C:34](B(O)O)=[CH:33][CH:32]=[N:31]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.O.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]>[O:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[N:30]1[C:34]([C:2]2[CH:3]=[C:4]3[C:13](=[CH:14][CH:15]=2)[C:12]2[N:8]([CH:9]=[C:10]([C:16]4[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:18][N:17]=4)[N:11]=2)[CH2:7][CH2:6][O:5]3)=[CH:33][CH:32]=[N:31]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 467394631-(Tetrahydropyran-2-yl)pyrazole-5-boronic acidHCID 582043138-bromo-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene

生成物 1

HCID 6831314112-[1-(oxan-2-yl)-1H-pyrazol-5-yl]-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene収率 92.5%

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
100 °C

実験手順

A mixture of 12-bromo-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (2.00 g, 5.34 mmol), 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-ylboronic acid (1.58 g, 8.01 mmol), Pd(dppf)Cl2 (437 mg, 0.535 mmol), Na2CO3 (1.70 g, 16.0 mmol) in DME/EtOH/H2O (15/3/3 mL) was stirred at 100° C. for 1 hr under microwave irradiation. The mixture was extracted with EtOAc, washed with brine, dried over MgSO4, filtered, and evaporated to give crude product, which was purified by silica gel chromatography eluting with EtOAc/petroleum ether (1:5) to afford 12-[1-(oxan-2-yl)-1H-pyrazol-5-yl]-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (2.2 g, 90% yield) as white solid. LCMS (ESI) m/z: 446.3 [M+H+].

後処理

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give crude product, which
  7. customwas purified by silica gel chromatography
  8. washeluting with EtOAc/petroleum ether (1:5)

出典と根拠

ORDレコード
ord-c19389f56872478ab48344a234a42531
出典データセット
uspto-grants-2015_07
特許番号
US09090628B2

反応ノート

読み込み中…