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Water → HCID 86653304, 화합물

HRID 1695746
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HRID 1695746 반응식
Br[C:2]1[CH:3]=[C:4]([NH2:12])[C:5]2[CH:6]=[N:7][N:8]([CH3:11])[C:9]=2[CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:19][C:20]1[N:25]=[CH:24][C:23](B(O)O)=[CH:22][C:21]=1[NH:29][S:30]([CH3:33])(=[O:32])=[O:31].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:12][C:4]1[CH:3]=[C:2]([C:23]2[CH:22]=[C:21]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[C:20]([Cl:19])=[N:25][CH:24]=2)[CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[CH3:11]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 582557716-Bromo-1-methyl-1h-indazol-4-amineHCID 86653303{6-Chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}boronic acid

생성물 1

HCID 86653304HCID 86653304, 화합물수율 29.9%

시약·촉매·용매 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

6-Bromo-1-methyl-1H-indazol-4-amine (340 mg), sodium carbonate (638 mg) and Pd(dppf)Cl2 (110 mg) were weighed to a 10-20 ml microwave vial. {6-Chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}boronic acid (377 mg) dissolved in 1,4-dioxane (6 ml) was added followed by water (6 ml). The reaction was heated for 15 min at 120° C. in the microwave. The reaction was passed through a 2 g silica cartridge, washing with methanol. The solvent was evaporated under nitrogen blow down. The residue was purified on the ISCO companion using a 40 g silica cartridge and a gradient of 2-8% methanol in DCM (containing 1% ammonia) over 15 mins at 40 ml/min. Product-containing fractions were combined and dried down to give title compound (158 mg).

후처리

  1. additionwas added
  2. washwashing with methanol
  3. customThe solvent was evaporated under nitrogen blow down
  4. customThe residue was purified on the ISCO companion
  5. customdried down

출처 및 근거

ORD 기록
ord-96256255827443ccadac58741674420a
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163743B2

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