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Sodium Carbonate → 4-{5-[2-(3,4-Dimethoxy-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-3-trifluoromethyl-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester

HRID 2409558
ノート
印刷プレビュー

反応式

HRID 2409558 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:15][C:14]3=[N:16][CH:17]=[C:18](I)[N:13]3[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][C:36](B3OC(C)(C)C(C)(C)O3)=[CH:35][N:34]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[C:20]([O:24][C:25]([N:27]1[CH2:28][CH2:29][N:30]([C:33]2[C:38]([C:39]([F:42])([F:40])[F:41])=[CH:37][C:36]([C:18]3[N:13]4[C:14]([S:15][C:11]([C:5]5[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=5)=[N:12]4)=[N:16][CH:17]=3)=[CH:35][N:34]=2)[CH2:31][CH2:32]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]
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

5

反応物 3

HCID 10340Sodium CarbonateHCID 667169462-(3,4-Dimethoxy-phenyl)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazoleHCID 66717282Tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-yl)piperazine-1-carboxylate

生成物 1

HCID 672838244-{5-[2-(3,4-Dimethoxy-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-3-trifluoromethyl-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester収率 56%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

A mixture of 2-(3,4-dimethoxy-phenyl)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole (0.2 g, 0.517 mmol, 1 eq), PdCl2(Ph3P)2 (73 mg, 0.103 mmol, 0.2 eq), 4-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.354 g, 0.775 mmol, 1.5 eq) and Na2CO3 (2M aqueous solution, 1 mL) in dioxane (4 mL) was heated at 110° C. for 2.5 h. The reaction was cooled down to rt and solvents were removed under reduced pressure. The residue was treated with water, sonicated and filtered. The solid was washed with water and purified by column chromatography (Biotage, cHex/EtOac 10 to 100%) to afford the desired product (170 mg, 56%): HPLC-MS: (5-100% B in 8 min, 0.8 mL/min, 50° C.): tR=7.36 min, [M+H]+ m/z 591.2; 1H NMR (300 MHz, CDCl3) δ 8.98 (d, J=2.0 Hz, 1H), 8.56 (d, J=2.2 Hz, 1H), 7.62 (s, 1H), 7.42 (m, 2H), 6.95 (m, 1H), 3.98 (s, 3H), 3.96 (s, 3H), 3.57 (m, 4H), 3.31 (m, 4H), 1.50 (s, 9H).

後処理

  1. temperatureThe reaction was cooled down to rt
  2. customsolvents were removed under reduced pressure
  3. additionThe residue was treated with water
  4. customsonicated
  5. filtrationfiltered
  6. washThe solid was washed with water
  7. custompurified by column chromatography (Biotage, cHex/EtOac 10 to 100%)

出典と根拠

ORDレコード
ord-0bcc95770e474fe0b868d30386b978b9
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08815918B2

反応ノート

読み込み中…

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