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Sodium Bicarbonate → N-{3-[(E)-2-(4-chlorophenyl)vinyl]-1H-indazol-5-yl}-2-methylsulfonylbenzenesulfonamide

HRID 25430
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HRID 25430 반응식
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[S:21]([CH3:24])(=[O:23])=[O:22])(=[O:14])=[O:13])[CH:9]=2)[N:4](C(OC(C)(C)C)=O)[N:3]=1.[Cl:32][C:33]1[CH:38]=[CH:37][C:36](/[CH:39]=[CH:40]/B(O)O)=[CH:35][CH:34]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:32][C:33]1[CH:38]=[CH:37][C:36](/[CH:39]=[CH:40]/[C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([NH:11][S:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[S:21]([CH3:24])(=[O:22])=[O:23])(=[O:13])=[O:14])[CH:9]=3)[NH:4][N:3]=2)=[CH:35][CH:34]=1
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5

반응물 3

HCID 516892Sodium BicarbonateHCID 642694trans-2-(4-Chlorophenyl)vinylboronic acidHCID 22567134Tert-butyl 3-iodo-5-(2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate

생성물 1

HCID 22567211N-{3-[(E)-2-(4-chlorophenyl)vinyl]-1H-indazol-5-yl}-2-methylsulfonylbenzenesulfonamide수율 65.8%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

N-{3-[(E)-2-(4-Chlorophenyl)vinyl]-1H-indazol-5-yl}-2-methylsulfonylbenzenesulfonamide can be obtained as described in Example 59 from 1 g of tert-butyl 3-iodo-5-(2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate, 631 mg of trans-2-(4-chlorophenyl) vinylboronic acid, 28 ml of dimethylformamide, 3.25 ml of a saturated aqueous sodium hydrogencarbonate solution and 48 mg of tetrakis(triphenylphosphine)-palladium[0]. 556 mg of N-{3-[(E)-2-(4-chlorophenyl)vinyl]-1H-indazol-5-yl}-2-methylsulfonylbenzenesulfonamide are thus obtained in the form of a pale yellow solid melting at 247° C. (analysis C22H18ClN3O4S2 % calculated C, 54.15; H, 3.72; Cl, 7.27; N, 8.61; O, 13.11; S, 13.14. % found C, 54.32; H, 4.40; Cl, 5.65; N, 7.83; S, 11.93).

출처 및 근거

ORD 기록
ord-9b4715c404514c328573927d8443caae
출처 데이터셋
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06858638B2

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