Cesium carbonate → 3-(6-Methoxypyridin-3-yl)-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine

HRID 573327ノート

反応式

HRID 573327 の反応式
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]([CH:11]([CH3:13])[CH3:12])[N:3]=1.[CH3:14][O:15][C:16]1[N:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:14][O:15][C:16]1[N:21]=[CH:20][C:19]([C:2]2[C:6]3=[N:7][CH:8]=[CH:9][CH:10]=[C:5]3[N:4]([CH:11]([CH3:13])[CH3:12])[N:3]=2)=[CH:18][CH:17]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 667280773-bromo-1-isopropyl-1H-pyrazolo[4,3-b]pyridine

生成物 1

HCID 866889833-(6-Methoxypyridin-3-yl)-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine収率 89.5%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 3-bromo-1-isopropyl-1H-pyrazolo[4,3-b]pyridine (100 mg), 6-methoxypyridin-3-ylboronic acid (96 mg), Pd(OAc)2 (9.35 mg), and Xphos (39.7 mg) in THF (3 mL) was added a solution of Cs2CO3 (271 mg) in H2O (1 mL). The mixture was exposed to microwave irradiation at 100° C. for 30 min, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (100 mg).

後処理

  1. customirradiation at 100° C. for 30 min
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

出典と根拠

ORDレコード
ord-c29caf5e70834c1f875e77dac3301b47
出典データセット
uspto-grants-2015_05
特許番号
US09029536B2

反応ノート

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