Potassium Carbonate → 1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-4-nitro-1H-indazole

HRID 706537ノート

反応式

HRID 706537 の反応式
O1[CH2:6][CH2:5]OCC1.BrC1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[N+:17]([O-:19])=[O:18])[N:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([CH3:29])[CH3:28])[N:22]=2)[N:9]=1.CB(O)O.C(=O)([O-])[O-].[K+].[K+]>O.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>[CH:27]([C:23]1[N:22]=[C:21]([CH2:20][N:10]2[C:11]3[C:16](=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][CH:12]=3)[C:5]([CH3:6])=[N:9]2)[CH:26]=[CH:25][CH:24]=1)([CH3:29])[CH3:28]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 139377Methylboronic Acid2 回HCID 679758823-bromo-1-((6-isopropylpyridin-2-yl)methyl)-4-nitro-1H-indazole

生成物 1

HCID 679762021-((6-isopropylpyridin-2-yl)methyl)-3-methyl-4-nitro-1H-indazole収率 73%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回

反応条件

温度
120 °C

実験手順

A 3 liter heavy walled reaction flask was charged with dioxane (1 liter), 3-bromo-1-((6-isopropylpyridin-2-yl)methyl)-4-nitro-1H-indazole (90 g, 0.24 mol), methyl boronic acid (72 g, 1.20 mol), Pd(PPh3)4 (9.7 g, 0.0084 mol), potassium carbonate (99.5 g, 0.719 mol), followed by 200 mL of water. This mixture was purged with argon for 10 minutes, flask sealed and heated to 120° C. for 16 hours. Another 1.5 mol % of Pd(PPh3)4 was added followed by another 2 equivalents of methyl boronic acid, and the mixture warmed to 120° C. for 24 hours. The mixture was diluted with water and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate and concentrated. Column chromatography (5% ethyl acetate/hexane to 10% ethyl acetate/hexane) gave 54 g (73%) of 1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-4-nitro-1H-indazole as an orange/yellow solid.

後処理

  1. customThis mixture was purged with argon for 10 minutes
  2. customflask sealed
  3. additionAnother 1.5 mol % of Pd(PPh3)4 was added
  4. temperaturethe mixture warmed to 120° C. for 24 hours
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-68ba87c1860c4ec78574a717269daca9
出典データセット
uspto-grants-2015_11
特許番号
US09174981B2

反応ノート

読み込み中…