2-Bromopyridine → 3-{1-(1,3-Benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1-methyl-6-(2-pyridylcarbonyl)-1H-indole

HRID 369354ノート

反応式

HRID 369354 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.CON(C)[C:16]([C:18]1[CH:26]=[C:25]2[C:21]([C:22]([CH:28]([C:42]3[CH:50]=[CH:49][C:45]4[O:46][CH2:47][O:48][C:44]=4[CH:43]=3)[C:29]([NH:31][S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])=[O:30])=[CH:23][N:24]2[CH3:27])=[CH:20][CH:19]=1)=[O:17]>O1CCCC1>[O:46]1[C:45]2[CH:49]=[CH:50][C:42]([CH:28]([C:22]3[C:21]4[C:25](=[CH:26][C:18]([C:16]([C:7]5[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=5)=[O:17])=[CH:19][CH:20]=4)[N:24]([CH3:27])[CH:23]=3)[C:29]([NH:31][S:32]([C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=3)(=[O:34])=[O:33])=[O:30])=[CH:43][C:44]=2[O:48][CH2:47]1

参加物

5

反応物 3

HCID 79732-BromopyridineHCID 22467206N6-methoxy-N6,1-dimethyl-3-{1-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1H-6-indolecarboxamideHCID 178418339Butyllithium

生成物 1

HCID 224672383-{1-(1,3-Benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1-methyl-6-(2-pyridylcarbonyl)-1H-indole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

n-Butyllithium (0.32 ml of 2.5M solution in hexane) was added to a stirred solution of 2-bromopyridine (0.08 ml, 0.8 mmol) in anhydrous tetrahydrofuran (5 ml) at -70° C. under a nitrogen atmosphere. After 30 minutes a solution of N6-methoxy-N6,1-dimethyl-3-{1-(1,3-benzodioxol-5yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1H-6-indolecarboxamide (the compound of Example 103, 200 mg, 0.36 mmol) in anhydrous tetrahydrofuran (2 ml) was added to the mixture at -70° C. The mixture was stirred at -70° C. for an additional 4 hours before being warmed to 0° C. and then quenched with the addition of water (5 ml). The mixture was acidified with acetic acid, and extracted with ethyl acetate (100 ml). The organic phase was separated and washed with brine, dried (magnesium sulphate) and the solvent was removed in vacuo. The residue was flash chromatographed using a gradient elution of a mixture of 90% hexane and 10% ethyl acetate, through to 100% ethyl acetate, to give the title compound (42 mg).

後処理

  1. temperaturebefore being warmed to 0° C.
  2. customquenched with the addition of water (5 ml)
  3. extractionextracted with ethyl acetate (100 ml)
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried (magnesium sulphate)
  7. customthe solvent was removed in vacuo
  8. customchromatographed
  9. washa gradient elution of a mixture of 90% hexane and 10% ethyl acetate

出典と根拠

ORDレコード
ord-342070f8b0c14fb6b991ca9bcd792a93
出典データセット
uspto-grants-2000_10
特許番号
US06136843

反応ノート

読み込み中…