Potassium Carbonate → HCID 59320215、化合物

HRID 655282

反応式

HRID 655282 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]1[N:17]3[N:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]3=[N:15][N:14]=1)=[CH:7][CH:6]=2.[CH3:23][N:24]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[N:25]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH3:23][N:24]1[CH:28]=[C:27]([C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][C:8]([CH2:12][C:13]2[N:17]4[N:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]4=[N:15][N:14]=2)=[CH:7][CH:6]=3)[CH:26]=[N:25]1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 593202953-Bromo-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline

生成物 1

HCID 59320215HCID 59320215、化合物収率 4%

試薬・触媒・溶媒 3

HCID 53485975CID 53485975触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 3-bromo-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline (50 mg, 0.141 mmol, 1.0 equiv.) in 1,4-dioxane (1 mL) was degassed with nitrogen and added to a microwave tube containing 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.177 mmol, 1.25 equiv., 37 mg). A degassed solution of potassium carbonate (0.282 mmol, 2 equiv., 39 mg) in water (0.5 mL) was then added to the microwave tube followed by dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (5 mg, 0.0071 mmol, 0.05 equiv). The microwave tube was capped and reacted in a microwave reactor at 100° C. for 30 minutes. The reaction mixture was partitioned between dichloromethane and water, and the organic layer was evaporated and the residue directly adsorbed on silica gel. Purification on silica gel with 0-10% gradient of methanol in dichloromethane, followed by trituration with methanol afforded the title compound (1.8 mg, 0.005 mmol, 4% yield) as a white solid. Analytical data presented in Table 2.

後処理

  1. additionadded to a microwave tube
  2. customThe microwave tube was capped
  3. customreacted in a microwave reactor at 100° C. for 30 minutes
  4. customThe reaction mixture was partitioned between dichloromethane and water
  5. customthe organic layer was evaporated
  6. customPurification on silica gel with 0-10% gradient of methanol in dichloromethane

出典と根拠

ORDレコード
ord-e78c386123dd46f984c1be40fe3cec6a
出典データセット
uspto-grants-2011_12
特許番号
US08071581B2

関連ノート

読み込み中…