Sodium Bicarbonate → N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide

HRID 1452906

反応式

HRID 1452906 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: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][CH:47]=3)(=[O:45])=[O:44])C(OC(C)(C)C)=O)[CH:33]=2)[N:28](C(OC(C)(C)C)=O)[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][CH:47]=3)(=[O:44])=[O:45])[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 68877978tert-butyl 3-iodo-5-(N-tert-butoxycarbonylbenzenesulfonylamino)indazole-1-carboxylate

生成物 1

HCID 135621938N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide収率 66.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
122 °C

実験手順

N-[3-(1H-Indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide can be obtained in the following way: 158.1 mg of N-tert-butoxycarbonylindole-2-boronic acid and 360 μl of a saturated sodium hydrogencarbonate solution and then 48.2 mg of tetrakis(triphenyl-phosphine)palladium[0] are added to a solution of 101.9 mg of tert-butyl 3-iodo-5-(N-tert-butoxycarbonylbenzenesulfonylamino)indazole-1-carboxylate in 4.5 ml of dimethylformamide. The suspension is heated in the region of 122° C. for 16 hours. After cooling to a temperature in the region of 20° C., the catalyst is filtered through a bed of Celite® 535, and the filtrate is concentrated to dryness under reduced pressure. The reaction crude is purified by preparative HPLS chromatography coupled to a mass detector (LC/MS, conditions A). The fractions containing the expected product are pooled and concentrated. 43.8 mg of N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide are obtained in the form of the trifluoroacetate salt (LC/MS analysis: Tr=3.49 minutes; [M+H]+=389.13).

後処理

  1. temperatureAfter cooling to a temperature in the region of 20° C.
  2. filtrationthe catalyst is filtered through a bed of Celite® 535
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure
  4. customThe reaction crude
  5. customis purified by preparative HPLS chromatography
  6. additionThe fractions containing the expected product
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-f51e5c9af9ba43b2aca6bb9680712a7d
出典データセット
uspto-grants-2009_01
特許番号
US07473701B2

関連ノート

読み込み中…