Cesium carbonate → 3-(1-Isopropyltriazol-4-yl)-5-[3-(morpholinomethyl)phenyl]pyridin-2-amine

HRID 632496ノート

反応式

HRID 632496 の反応式
C([O-])([O-])=O.[Cs+].[Cs+].[O:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=2)[CH2:9][CH2:8]1.Br[C:24]1[CH:25]=[C:26]([C:31]2[N:32]=[N:33][N:34]([CH:36]([CH3:38])[CH3:37])[CH:35]=2)[C:27]([NH2:30])=[N:28][CH:29]=1>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>[CH:36]([N:34]1[CH:35]=[C:31]([C:26]2[C:27]([NH2:30])=[N:28][CH:29]=[C:24]([C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([CH2:13][N:10]4[CH2:11][CH2:12][O:7][CH2:8][CH2:9]4)[CH:15]=3)[CH:25]=2)[N:32]=[N:33]1)([CH3:38])[CH3:37]

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 110314093-(Morpholinomethyl)phenylboronic acidHCID 902731555-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyridin-2-ylamine

生成物 1

HCID 771065593-(1-Isopropyltriazol-4-yl)-5-[3-(morpholinomethyl)phenyl]pyridin-2-amine収率 58.5%

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
120 °C

実験手順

Cs2CO3 (858 mg, 2.64 mmol) was added to a solution of (3-(morpholinomethyl)phenyl)boronic acid (250 mg, 0.88 mmol) and 5-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyridin-2-ylamine (215 mg, 0.97 mmol) in dioxane: water (8 mL: 4 mL) degassed the reaction mixture for 10 min with nitrogen. Then added Pd(PPh3)4 (50 mg, 0.044 mmol), degassed the reaction mixture for additional 10 min with nitrogen, the reaction mixture was heated to 120° C. in microwave for 1 h. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×30 mL). Combined organic layers was dried over Na2SO4 and concentrated under reduced pressure. Crude product was purified by silica (100-200 mesh) column eluted with 80-90% ethyl acetate in pet-ether to afford 195 mg (Yield: 58.13%) of the title compound as a pale yellow solid. Product was converted to its HCl salt by using HCl in ether (2M) to afford 202 mg as a pale yellow solid.

後処理

  1. customwater (8 mL: 4 mL) degassed the reaction mixture for 10 min with nitrogen
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. dry with materialCombined organic layers was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customCrude product was purified by silica (100-200 mesh) column
  6. washeluted with 80-90% ethyl acetate in pet-ether

出典と根拠

ORDレコード
ord-1258ea03659144808d20bd1fdc97041d
出典データセット
uspto-grants-2016_04
特許番号
US09321748B2

反応ノート

読み込み中…