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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 490459
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HRID 490459 반응식
[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
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참가 물질

5

반응물 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]-

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
110 °C

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-acc61733f0be464bb8fbfade83e1f15b
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07528147B2

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