Cesium carbonate → 1-(4-methoxybenzyl)-5-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 715045ノート

反応式

HRID 715045 の反応式
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[C:15](B4OC(C)(C)C(C)(C)O4)[CH:16]=[C:11]3[CH:10]=[CH:9]2)=[CH:5][CH:4]=1.Br[C:29]1[CH:42]=[CH:41][C:32]([CH2:33][N:34]2[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]2)=[CH:31][CH:30]=1.C([O-])([O-])=O.[Cs+].[Cs+]>COCCOC.C(Cl)Cl.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>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:42]4[CH:29]=[CH:30][CH:31]=[C:32]([CH2:33][N:34]5[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]5)[CH:41]=4)[CH:16]=[C:11]3[CH:10]=[CH:9]2)=[CH:26][CH:27]=1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 221976121-[(4-Bromophenyl)methyl]-4-methylpiperazineHCID 683884711-(4-methoxybenzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 683884751-(4-methoxybenzyl)-5-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridine

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

A stirred solution of 1-(4-methoxybenzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (147PG) (50 mg, 0.137 mmol) and 1-(4-bromobenzyl)-4-methylpiperazine (121) (37 mg, 0.137 mmol, 1.1 eq) in DME (10 mL) was degassed and purged with N2 for 10 min and Cs2CO3 (2.0 eq) was added and the reaction mixture purged and degassed again. To this reaction mixture was added Pd(PPh3)4 (0.04 eq) and the resulting reaction was heated at 90° C. for 12 hrs in sealed tube condition. After completion of the reaction the contents were was cooled and diluted with CH2Cl2 and filtered through Celite bed. The CH2Cl2 layer was completely distilled off to get the crude product. The crude was passed through 100-200 mesh silica gel, eluting the pure compound 1-(4-methoxybenzyl)-5-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridine 151 obtained with 5% MeOH in CH2Cl2 as an off-white coloured solid in 30 mg quantity.

後処理

  1. custompurged with N2 for 10 min
  2. customthe reaction mixture purged
  3. customdegassed again
  4. customthe resulting reaction
  5. customAfter completion of the reaction the contents
  6. temperaturewere was cooled
  7. filtrationfiltered through Celite bed
  8. distillationThe CH2Cl2 layer was completely distilled off
  9. customto get the crude product
  10. washeluting the pure compound 1-(4-methoxybenzyl)-5-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridine 151
  11. customobtained with 5% MeOH in CH2Cl2 as an off-white coloured solid in 30 mg quantity

出典と根拠

ORDレコード
ord-44be677384114cde8f0c5dd51f09be20
出典データセット
uspto-grants-2015_11
特許番号
US09187473B2

反応ノート

読み込み中…