Potassium Carbonate → HCID 86700054、化合物

HRID 1428103ノート

反応式

HRID 1428103 の反応式
[CH3:1][O:2][C:3]1[CH:16]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:14]=[CH:13][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].[Br:32][C:33]1[C:34]([NH2:40])=[N:35][CH:36]=[C:37](I)[CH:38]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:32][C:33]1[C:34]([NH2:40])=[N:35][CH:36]=[C:37]([C:15]2[CH:14]=[CH:13][C:4]([O:5][CH2:6][CH2:7][N:8]3[CH2:9][CH2:10][CH2:11][CH2:12]3)=[C:3]([O:2][CH3:1])[CH:16]=2)[CH:38]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 176094413-Bromo-5-iodopyridin-2-amineHCID 68934529HCID 68934529、化合物

生成物 1

HCID 86700054HCID 86700054、化合物収率 61.4%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

1-{2-[2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl}pyrrolidine (5.81 g), tetrakis(triphenylphosphine)palladium (0.97 g) and potassium carbonate (6.94 g) were added to a solution of 3-bromo-5-iodopyridin-2-amine (5.00 g) in dioxane (40 ml) and water (4 ml) at room temperature. The reaction mixture was stirred at 80° C. overnight. The reaction mixture was returned to room temperature and a saturated aqueous sodium bicarbonate solution was added, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=50:1->20:1->10:1 (v/v)] to give 4.03 g of the title compound as an oily substance.

後処理

  1. customwas returned to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [chloroform:methanol=50:1->20:1->10:1 (v/v)]

出典と根拠

ORDレコード
ord-3f538baf6e22472cb49e0cb81c7e88bc
出典データセット
uspto-grants-2015_01
特許番号
US08933103B2

反応ノート

読み込み中…