Cesium carbonate → HCID 67271616、化合物

HRID 1696474ノート

反応式

HRID 1696474 の反応式
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

参加物

7

反応物 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)

生成物 1

HCID 67271616HCID 67271616、化合物収率 76%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-4babff8357594ae2a7b19f34bf0b8bd3
出典データセット
uspto-grants-2012_04
特許番号
US08163756B2

反応ノート

読み込み中…