Cesium carbonate → HCID 67271616, 화합물

HRID 1696474노트

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HRID 1696474 반응식
Cl.Br[C:3]1[CH:4]=[C:5]([N:9]2[C:13]([NH2:14])=[CH:12][C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[N:29][N:30](C(OC(C)(C)C)=O)[CH:31]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[NH:29]1[CH:28]=[C:27]([C:3]2[CH:4]=[C:5]([N:9]3[C:13]([NH2:14])=[CH:12][C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])=[N:10]3)[CH:6]=[CH:7][CH:8]=2)[CH:31]=[N:30]1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 534073321-(3-Bromophenyl)-3-tert-butyl-1H-pyrazol-5-amine--hydrogen chloride (1/1)

생성물 1

HCID 67271616HCID 67271616, 화합물수율 76%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매2회HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A solution of 1-(3-bromophenyl)-3-t-butyl-1H-pyrazol-5-amine hydrochloride (0.253 g, 0.77 mmol, available from Example 54), t-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (0.28 g, 0.95 mmol, commercially available) and Cs2CO3 (1.0 g, 3.1 mmol) in DMF (5 mL) and H2O (2 mL) was placed under Ar for 15 min. Palladium tetrakis(triphenylphosphine) was added and the reaction mixture was heated at 80° C. overnight. The reaction mixture was poured into H2O (20 mL) and extracted with EtOAc (2×30 mL). The extracts were washed with H2O (10 mL) and brine (10 mL), dried (Na2SO4) concentrated and purified via column chromatography to yield 1-(3-(1H-pyrazol-4-yl)phenyl)-3-t-butyl-1H-pyrazol-5-amine (163 mg, 76% yield). MS (ESI) m/z: 282.3 (M+H+).

후처리

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe extracts were washed with H2O (10 mL) and brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography

출처 및 근거

ORD 기록
ord-4babff8357594ae2a7b19f34bf0b8bd3
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163756B2

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