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Sodium Bicarbonate → 2-(5,6-dimethoxy-1H-indol-3-yl)-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 2426855
ノート
印刷プレビュー

反応式

HRID 2426855 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9](I)[N:8]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.C(OC([N:29]1[C:37]2[C:32](=[CH:33][C:34]([O:40][CH3:41])=[C:35]([O:38][CH3:39])[CH:36]=2)[C:31](B(O)O)=[CH:30]1)=O)(C)(C)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:41][O:40][C:34]1[CH:33]=[C:32]2[C:37](=[CH:36][C:35]=1[O:38][CH3:39])[NH:29][CH:30]=[C:31]2[C:9]1[N:8]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=[C:2]([F:1])[CH:3]=[C:4]2[CH:10]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 671474461-tert-butyloxycarbonyl-5,6-dimethoxy-1H-indole-3-boronic acidHCID 671475501H-Pyrrolo[2,3-b]pyridine, 5-fluoro-2-iodo-1-[(4-methylphenyl)sulfonyl]-

生成物 1

HCID 671475792-(5,6-dimethoxy-1H-indol-3-yl)-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine収率 76.7%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
110 °C

実験手順

A mixture of 3.1 g of 5-fluoro-2-iodo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine, 2.4 g of 1-tert-butyloxycarbonyl-5,6-dimethoxy-1H-indole-3-boronic acid and 20.3 ml of a saturated aqueous sodium hydrogen carbonate solution in 100 ml of dimethylformamide is degassed with argon for approximately 15 minutes and then 0.43 g of tetrakis(triphenylphosphine)palladium is added. The mixture is heated at around 110° C. for approximately 2 hours and then concentrated to dryness under reduced pressure (13 kPa). The residue is taken up with 500 ml of water, and extracted with three times 250 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered, and concentrated to dryness under reduced pressure. The residue is taken up with 100 ml of diisopropyl ether, filter-dried, washed with three times 20 ml of diisopropyl ether, and dried under reduced pressure (13 kPa) in the presence of potassium hydroxide chips at a temperature in the region of 20° C. 2.66 g of 2-(5,6-dimethoxy-1H-indol-3-yl)-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine are obtained in the form of a solid, the characteristics of which are as follows:

後処理

  1. customis degassed with argon for approximately 15 minutes
  2. addition0.43 g of tetrakis(triphenylphosphine)palladium is added
  3. concentrationconcentrated to dryness under reduced pressure (13 kPa)
  4. extractionextracted with three times 250 ml of ethyl acetate
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customfilter-dried
  9. washwashed with three times 20 ml of diisopropyl ether
  10. dry with materialdried under reduced pressure (13 kPa) in the presence of potassium hydroxide chips at a temperature in the region of 20° C

出典と根拠

ORDレコード
ord-61b9dcfd2291417aab934280adf47fcb
出典データセット
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07968566B2

反応ノート

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