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Potassium Phosphate, Tribasic → 3-(3-bromo-5-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

HRID 1524409
ノート
印刷プレビュー

反応式

HRID 1524409 の反応式
[CH3:1][O:2][C:3]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:4]=1[CH2:5][N:6]([C:29]1[S:33][N:32]=[CH:31][N:30]=1)[S:7]([C:10]1[CH:18]=[C:17]2[C:13]([C:14](B3OC(C)(C)C(C)(C)O3)=[CH:15][N:16]2[CH3:19])=[CH:12][CH:11]=1)(=[O:9])=[O:8].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Br:48][C:49]1[CH:54]=[C:53]([C:55]([F:58])([F:57])[F:56])[CH:52]=[C:51](Br)[CH:50]=1>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].C(Cl)Cl.CN(C=O)C>[Br:48][C:49]1[CH:50]=[C:51]([C:14]2[C:13]3[C:17](=[CH:18][C:10]([S:7]([N:6]([CH2:5][C:4]4[CH:34]=[CH:35][C:36]([O:38][CH3:39])=[CH:37][C:3]=4[O:2][CH3:1])[C:29]4[S:33][N:32]=[CH:31][N:30]=4)(=[O:9])=[O:8])=[CH:11][CH:12]=3)[N:16]([CH3:19])[CH:15]=2)[CH:52]=[C:53]([C:55]([F:56])([F:57])[F:58])[CH:54]=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

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 20634891,3-Dibromo-5-(trifluoromethyl)benzeneHCID 71259251N-(2,4-dimethoxybenzyl)-1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

生成物 1

HCID 903882113-(3-bromo-5-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide収率 34.6%

試薬・触媒・溶媒

2
HCID 178418807HCID 178418807、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

A vial was charged with N-(2,4-dimethoxybenzyl)-1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (0.200 g, 0.351 mmol), potassium phosphate (0.260 g, 1.227 mmol), and PdCl2(dppf)-CH2Cl2 (0.029 g, 0.035 mmol). DMF (0.150 mL) was added, followed by 1,3-dibromo-5-(trifluoromethyl)benzene (0.166 ml, 1.052 mmol). The vial was flushed with argon, sealed, and stirred at 85° C. for two hours. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (silica gel, gradient elution 0 to 75% EtOAc:Hexane) to afford 3-(3-bromo-5-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (0.081 g, 0.121 mmol, 34.6% yield) as a white solid. m/z (ESI) 668.0 (M+H)+.

後処理

  1. customThe vial was flushed with argon
  2. customsealed
  3. additionThe reaction was diluted with ethyl acetate
  4. washwashed with water
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe material was purified via column chromatography (silica gel, gradient elution 0 to 75% EtOAc:Hexane)

出典と根拠

ORDレコード
ord-a85f1d6b12b04964aa45c8c3ee559aa2
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09079902B2

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