Cesium carbonate → 2-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-6-[methyl-(toluene-4-sulfonyl)-amino]-indole-1-carboxylic acid tert-butyl ester

HRID 2234119ノート

反応式

HRID 2234119 の反応式
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[CH:10]=[C:9]1[C:18]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[N:21]=[N:20][C:19]=1[O:30][CH3:31])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:32][NH:33][S:34]([C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=1)(=[O:36])=[O:35].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N:33]([CH3:32])[S:34]([C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=3)(=[O:36])=[O:35])[CH:15]=2)[CH:10]=[C:9]1[C:18]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[N:21]=[N:20][C:19]=1[O:30][CH3:31])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 12543Benzenesulfonamide, N,4-dimethyl-HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 686373616-Bromo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester

生成物 1

HCID 686370322-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-6-[methyl-(toluene-4-sulfonyl)-amino]-indole-1-carboxylic acid tert-butyl ester収率 37.5%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
130 °C

実験手順

Under argon, 340 mg 6-Bromo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester (see example 132), 157 mg N-methyl-para-toluenesulfonamide, 322 mg cesium carbonate, 32 mg Pd2(dba)3, and 30 mg xantphos are dissolved in 6.8 mL toluene. Argon is bubbled through the solution for 5 minutes. The reaction mixture is heated to 130° C. for 1 hour in a microwave oven. Then the reaction mixture is diluted with EtOAc and washed with water. The organic phase is dried (MgSO4) and the solvent removed in vacuo. Purification by HPLC affords 155 mg (37%) 2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-6-[methyl-(toluene-4-sulfonyl)-amino]-indole-1-carboxylic acid tert-butyl ester.

後処理

  1. customArgon is bubbled through the solution for 5 minutes
  2. additionThen the reaction mixture is diluted with EtOAc
  3. washwashed with water
  4. dry with materialThe organic phase is dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customPurification by HPLC

出典と根拠

ORDレコード
ord-fa6775ac077c4d31bbcfeeb15f0bd174
出典データセット
uspto-grants-2010_05
特許番号
US07709466B2

反応ノート

読み込み中…