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Potassium Carbonate → HCID 86711935、化合物

HRID 1475243
ノート
印刷プレビュー

反応式

HRID 1475243 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[N:9][C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[N:13]=2)=[N:7]1.[CH2:31]([Sn](CCCC)(CCCC)C=C)[CH2:32]CC.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[CH:31]([C:2]1[CH:3]=[C:4]([CH2:5][N:6]2[C:10]([CH3:11])=[N:9][C:8]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:25])[F:26])=[CH:19][CH:18]=4)[N:13]=3)=[N:7]2)[CH:28]=[CH:29][CH:30]=1)=[CH2:32]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 81998TributylvinyltinHCID 867119065-(1-(3-bromobenzyl)-5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole

生成物 1

HCID 86711935HCID 86711935、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31275
1,4-Dioxane
溶媒

反応条件

温度
110 °C

実験手順

To a mixture of 5-(1-(3-bromobenzyl)-5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (Example 11, Step 1; 200 mg, 0.42 mmol), tributyl(vinyl)stannane (159 mg, 0.50 mmol) and K2CO3 (174 mg, 1.26 mmol) in 1,4-dioxane (5 mL), was added Pd(PPh4)3 (28 mg, 0.025 mmol). The reaction mixture was heated in a sealed vial at 110° C. under inert atmosphere for 12 h, cooled to RT, diluted with H2O (30 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with H2O (10 mL) and brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure; the residue was purified by prep-HPLC to give the title compound as a white solid; MS (ES+) C21H16F3N5O2 requires: 427. found: 428 [M+H]+; 1H-NMR (500 MHz, DMSO-d6) δ 8.22 (d, J=9 Hz, 2H), 7.61 (d, J=9 Hz, 2H), 7.48 (d, J=7 Hz, 1H), 7.43 (s, 1H), 7.38 (m, 1H), 7.21 (d, J=7 Hz, 1H), 6.76 (m, 1H), 5.87 (d, J=17.5 Hz, 1H), 5.57 (s, 2H), 5.31 (d, J=11.5 Hz, 1H), 2.60 (s, 3H).

後処理

  1. temperaturecooled to RT
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic layers were washed with H2O (10 mL) and brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by prep-HPLC

出典と根拠

ORDレコード
ord-4f09069823454ecf9a462de6f1204885
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09018380B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート