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Dimethylformamide → N-{5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-chloro-3-pyridinyl}methanesulfonamide

HRID 1695731
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HRID 1695731 반응식
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[C:16]([Sn](C)(C)C)[CH:15]=[C:14]([NH2:23])[C:13]=3[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.Br[C:30]1[CH:31]=[C:32]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[C:33]([Cl:36])=[N:34][CH:35]=1>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:23][C:14]1[CH:15]=[C:16]([C:30]2[CH:31]=[C:32]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[C:33]([Cl:36])=[N:34][CH:35]=2)[CH:17]=[C:18]2[C:13]=1[CH:12]=[N:11][N:10]2[S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8]
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참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 582557431-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amineHCID 59519513N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamide

생성물 1

HCID 58255829N-{5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-chloro-3-pyridinyl}methanesulfonamide수율 19.8%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6344Dichloromethane용매

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온도
120 °C

실험 절차

Four identical reactions were carried out in a 20 ml microwave vial, each using one quarter of the quantities stated. They were then combined for work-up and purification. A solution of a quarter of 1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (4.329 g, 9.93 mmol) in a quarter of DMF (24 ml) was treated with a quarter of N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamide (3.26 g, 11.42 mmol) followed by a quarter of Pd(PPh3)4 (1.032 g, 0.893 mmol). Each vial was heated at 120° C. for 50 mins in a Biotage Initiator. The orange solutions were combined and loaded onto a 20 g silica cartridge, and the vials washed with methanol (10 ml) which was also loaded onto the cartridge which was then eluted with methanol. Then eluants were evaporated to leave an orange oil. This was diluted with DCM (10 ml) and loaded directly and evenly onto 2×100 g silica cartridges. These were eluted with 0-100% ethyl acetate/cyclohexane over 80 mins using the Flashmaster II. Appropriate pure fractions were combined and evaporated to give the title compound as a yellow solid (0.939 g).

후처리

  1. customThey were then combined for work-up and purification
  2. washthe vials washed with methanol (10 ml) which
  3. washwas then eluted with methanol
  4. customThen eluants were evaporated
  5. customto leave an orange oil
  6. washThese were eluted with 0-100% ethyl acetate/cyclohexane over 80 mins
  7. customevaporated

출처 및 근거

ORD 기록
ord-dc694676df0c4708888270c79301512f
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163743B2

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