Acetonitrile → 6-(Pyrrolidinylcarbonyl)-3-[4-(4-methylpiperizin-1-yl)-phenyl]-9H-dipyrido[2,3-b;4',3'-d]pyrrole

HRID 1506011ノート

反応式

HRID 1506011 の反応式
[N:1]1([C:6]([C:8]2[N:16]=[CH:15][C:14]3[NH:13][C:12]4[N:17]=[CH:18][C:19](Br)=[CH:20][C:11]=4[C:10]=3[CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:22](#[N:24])[CH3:23]>C(=O)([O-])[O-].[Na+].[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:1]1([C:6]([C:8]2[N:16]=[CH:15][C:14]3[NH:13][C:12]4[N:17]=[CH:18][C:19]([C:9]5[CH:10]=[CH:14][C:22]([N:24]6[CH2:4][CH2:5][N:1]([CH3:6])[CH2:2][CH2:3]6)=[CH:23][CH:8]=5)=[CH:20][C:11]=4[C:10]=3[CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 6342AcetonitrileHCID 582665346-(Pyrrolidinylcarbonyl)-3-bromo-9H-dipyrido[2,3-b:4',3'-d]pyrrole

生成物 1

HCID 582665466-(Pyrrolidinylcarbonyl)-3-[4-(4-methylpiperizin-1-yl)-phenyl]-9H-dipyrido[2,3-b;4',3'-d]pyrrole収率 5%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 10340Sodium Carbonate溶媒

反応条件

温度
120 °C

実験手順

A degassed mixture of 6-(pyrrolidinylcarbonyl)-3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (158 mg, 0.457 mmol), 4-(4-methylpiperizin-1-yl)-phenyl-1-boronic acid, pinacol ester (597 mg, 1.98 mmol), and bis(triphenylphosphine)palladium(II) chloride (69.0 mg, 99.0 μmol, 5.0 mol %) in acetonitrile (2.5 mL) and 1.0M aqueous sodium carbonate (2.5 mL) was heated under microwave irradiation at 120° C. for 10 minutes, allowed to cool, and partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate filtered and concentrated in vacuo. The resultant residue was purified by preparative HPLC (0-30% MeCN/water modified with 0.1% formic acid) to afford an off-white solid (10.0 mg, 5%). 1H NMR (DMSO-D6, 400 MHz) 12.39-12.29 (s, 1H), 9.01 (d, J=2.2 Hz, 1H), 8.88 (d, J=2.2 Hz, 31), 8.86 (s, 1H), 8.70 (s, 1H), 7.69 (d, J=8.7 Hz, 2H), 7.08 (d, J=8.8 Hz, 2H), 3.78 (t, J=6.2 Hz, 2H), 3.57 (t, J=6.2 Hz, 2H), 3.25-3.18 (m, 4H), 2.47 (m, 311), 2.24 (m, 4H), 1.87 (m, 4H). LCMS (Method D): RT=7.36 min, M+H+=441.

後処理

  1. temperatureto cool
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by preparative HPLC (0-30% MeCN/water modified with 0.1% formic acid)

出典と根拠

ORDレコード
ord-91943b5d8451408681edf7e854c3b541
出典データセット
uspto-grants-2015_12
特許番号
US09216980B2

反応ノート

読み込み中…