Tetrahydrofuran → 5-(4-Fluorophenyl)-3-(1-Methylpiperidin-4-yl)-4-Aza-1H-Indole

HRID 278003ノート

反応式

HRID 278003 の反応式
FC(F)(F)S(O[C:7]1[N:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)(=O)=O.[F:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(=O)(O)[O-].[Na+].O1CCCC1>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.C(Cl)(Cl)Cl>[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:7]2[N:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH:11]=[C:10]3[CH:16]2[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]2)=[CH:28][CH:27]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 2856454-Fluorophenylboronic acidHCID 516892Sodium BicarbonateHCID 120418125-Trifluoromethanesulfonyloxy-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-b]pyridine

生成物 1

HCID 98614675-(4-Fluorophenyl)-3-(1-Methylpiperidin-4-yl)-4-Aza-1H-Indole収率 69%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6212Chloroform溶媒

反応条件

温度
75 °C

実験手順

O-Trifluoromethanesulfonyl-3-(1-methylpiperidin-4-yl)-5-hydroxy-4-aza-1H-indole (150 mg, 0.412 mmol), 4-fluorophenylboronic acid (87 mg, 0.619 mmol), tetrakis(triphenylphosphine)palladium(0) (48 mg, 0.041 mmol), 4 mL of 2M aqueous sodium bicarbonate, and 30 mL of tetrahydrofuran were placed in a round bottom flask. The mixture was heated to reflux (about 75° C.) and allowed to stir for about 18 hours. The reaction was poured into 3:1 chloroform:isopropyl alcohol, extracted three times each with 1N aqueous sodium hydroxide and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed (silica gel, 0-10% methanol/dichloromethane) to give 87.9 mg of the title compound. (79%). MS(FD) m/e 309.6 (M+). EA calculated for C19H20FN3: C, 73.79; H, 6.47; N, 13.59. Found: C, 73.69; H, 6.73; N, 13.40.

後処理

  1. temperatureThe mixture was heated
  2. extractionisopropyl alcohol, extracted three times each with 1N aqueous sodium hydroxide and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed (silica gel, 0-10% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-14d97597f0f54c4e825e32ddaec5e856
出典データセット
uspto-grants-2002_03
特許番号
US06358972B1

反応ノート

読み込み中…