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Potassium Phosphate, Tribasic → N-(5-(2,6-difluorobenzyl)-1-methylpiperidin-3-yl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

HRID 1467340
ノート
印刷プレビュー

反応式

HRID 1467340 の反応式
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([NH:13][CH:14]3[CH2:19][CH:18]([CH2:20][C:21]4[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=4[F:28])[CH2:17][N:16]([CH3:29])[CH2:15]3)=[O:12])[CH:9]=2)[N:4]([C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:57][C:58]1[CH:63]=[C:62](B2OC(C)(C)C(C)(C)O2)[CH:61]=[CH:60][N:59]=1>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:27][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]([F:28])[C:21]=1[CH2:20][CH:18]1[CH2:17][N:16]([CH3:29])[CH2:15][CH:14]([NH:13][C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]([C:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[N:3]=[C:2]3[C:62]2[CH:61]=[CH:60][N:59]=[C:58]([CH3:57])[CH:63]=2)=[O:12])[CH2:19]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

5

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 164142742-Methylpyridine-4-boronic acid pinacol esterHCID 679965083-bromo-N-(5-(2,6-difluorobenzyl)-1-methylpiperidin-3-yl)-1-trityl-1H-indazole-5-carboxamide

生成物 1

HCID 70653003N-(5-(2,6-difluorobenzyl)-1-methylpiperidin-3-yl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

試薬・触媒・溶媒 1

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒

反応条件

温度
80 °C

実験手順

3-bromo-N-(5-(2,6-difluorobenzyl)-1-methylpiperidin-3-yl)-1-trityl-1H-indazole-5-carboxamide (0.050 g, 0.0716 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (0.0052 g, 0.00716 mmol), Potassium phosphate tribasic (0.046 g, 0.215 mmol) and 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.018 g, 0.0788 mmol) was added into a flask. After purging the reaction vessel with nitrogen gas, dioxane (0.215 mL) and water (0.043 mL) was added. The reaction was allowed to stir at 80° C. for 16 hrs. The reaction was quenched with water (1 mL) and extracted with dichloromethane (3×1 mL). The extracts were combined, dried using sodium sulfate, filtered through celite, and concentrated under vacuo. The crude product was progressed to the next step without further purification. LC-MS found 718.2, calcd M+H 718.3.

後処理

  1. customAfter purging the reaction vessel with nitrogen gas, dioxane (0.215 mL) and water (0.043 mL)
  2. additionwas added
  3. customThe reaction was quenched with water (1 mL)
  4. extractionextracted with dichloromethane (3×1 mL)
  5. customdried
  6. filtrationfiltered through celite
  7. concentrationconcentrated under vacuo
  8. customThe crude product was progressed to the next step without further purification

出典と根拠

ORDレコード
ord-a22383aa91e64f4583b726ecf591ef8f
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08999957B2

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