Sodium Bicarbonate → HCID 135621936、化合物

HRID 25439

反応式

HRID 25439 の反応式
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1B(O)O)=O)(C)(C)C.C(=O)([O-])O.[Na+].I[C:26]1(C(OC(C)(C)C)=O)[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([N:35]([S:43]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[O:52][C:53]([F:56])([F:55])[F:54])(=[O:45])=[O:44])C(OC(C)(C)C)=O)[CH:33]=2)[N:28]=[N:27]1>CN(C)C=O>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([NH:35][S:43]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[O:52][C:53]([F:54])([F:55])[F:56])(=[O:45])=[O:44])[CH:33]=2)[NH:28][N:27]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 27733021-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)HCID 22567356HCID 22567356、化合物

生成物 1

HCID 135621936HCID 135621936、化合物収率 58.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

N-[3-(1H-Indol-2-yl)-1H-indazol-5-yl]-2-trifluoromethoxybenzenesulfonamide can be obtained in the following way: 213.3 mg N-tert-butoxycarbonylindole-2-boronic acid in dimer form and 243 μl of a saturated sodium hydrogencarbonate solution and then 63.4 mg of tetrakis(triphenylphosphine)palladium[0] are added to a solution of 150 mg of tert-butyl 3-iodo-5-(N-tert-butoxycarbonyl-2-trifluoromethoxybenzenesulfonylamino)indazolecarboxylate in 4.5 ml of dimethylformamide. The suspension is heated in the region of 120° C. for 18 hours. After cooling to a temperature in the region of 20° C., the catalyst is filtered through sintered glass with Celite® 535, and the filtrate is concentrated to dryness under reduced pressure in a rotary evaporator. The reaction crude is purified by preparative HPLC chromatography coupled to a mass detector (LC/MS, conditions A). The fractions containing the expected product are pooled and concentrated, and then the base is released from the trifluoroacetate salt by being taken up in 10 ml of dichloromethane and washed with 10 ml of a saturated sodium hydrogencarbonate solution. The organic phase is dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure. 60.5 mg of N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]-2-trifluoromethoxy-benzenesulfonamide are thus obtained in the form of a white solid melting at 172-174° C. (analytical LC/MS analysis: Tr=3.73 minutes; [M+H]+=473.07).

後処理

  1. temperatureAfter cooling to a temperature in the region of 20° C.
  2. filtrationthe catalyst is filtered through sintered glass with Celite® 535
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure in a rotary evaporator
  4. customThe reaction crude
  5. customis purified by preparative HPLC chromatography
  6. additionThe fractions containing the expected product
  7. concentrationconcentrated
  8. washwashed with 10 ml of a saturated sodium hydrogencarbonate solution
  9. dry with materialThe organic phase is dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-4ecd565636464ee1a6ae4dacb0b0527b
出典データセット
uspto-grants-2005_02
特許番号
US06858638B2

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