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Sodium Carbonate → 3-(1-(2-Chlorophenyl)-1H-benzo[d][1,2,3]triazol-5-yl)-N-cyclopropyl-5-fluoro-4-methylbenzamide

HRID 1879448
ノート
印刷プレビュー

反応式

HRID 1879448 の反応式
[CH:1]1([NH:4][C:5](=[O:23])[C:6]2[CH:11]=[C:10](B3OC(C)(C)C(C)(C)O3)[C:9]([CH3:21])=[C:8]([F:22])[CH:7]=2)[CH2:3][CH2:2]1.Br[C:25]1[CH:40]=[CH:39][C:28]2[N:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:38])[N:30]=[N:31][C:27]=2[CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[N:29]1[C:28]2[CH:39]=[CH:40][C:25]([C:10]3[CH:11]=[C:6]([CH:7]=[C:8]([F:22])[C:9]=3[CH3:21])[C:5]([NH:4][CH:1]3[CH2:2][CH2:3]3)=[O:23])=[CH:26][C:27]=2[N:31]=[N:30]1
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

7

反応物 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 21914563N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 687701145-bromo-1-(2-chlorophenyl)-1H-benzo[d][1,2,3]triazole

生成物 1

HCID 252345383-(1-(2-Chlorophenyl)-1H-benzo[d][1,2,3]triazol-5-yl)-N-cyclopropyl-5-fluoro-4-methylbenzamide

試薬・触媒・溶媒

2
HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
125 °C

実験手順

To a mixture of N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (100 mg, 0.31 mmol), 5-bromo-1-(2-chlorophenyl)-1H-benzo[d][1,2,3]triazole (110 mg, 0.34 mmol), tetrakis(triphenylphosphine)palladium(0) (18 mg, 0.016 mmol) in dioxane (3 mL) was added 1.3 mL of 2 N sodium carbonate solution. The reaction mixture was heated at 125° C. in a microwave for 30 min. The mixture was then treated with 2 mL of 1 N NaOH and extracted with 2×15 mL of EtOAc. The combined organic phase was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography on silical gel (30-70% of EtOAc in Hexanes) to give the title compound as an off white crystalline solid. MS (ESI, pos. ion) m/z: 421.0 (M+1).

後処理

  1. extractionextracted with 2×15 mL of EtOAc
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude material was purified by flash chromatography on silical gel (30-70% of EtOAc in Hexanes)

出典と根拠

ORDレコード
ord-929ef3972a13410181088dc986c22196
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08314131B2

反応ノート

読み込み中…

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