Dimethylformamide → HCID 25120565、化合物

HRID 1640928ノート

反応式

HRID 1640928 の反応式
[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[C:20](B5OC(C)(C)C(C)(C)O5)=[CH:21][CH:22]=[CH:23][C:17]=4[CH:16]=3)[C:12]([F:33])=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1.Br[C:35]1[CH:40]=[CH:39][N:38]=[C:37]2[NH:41][CH:42]=[CH:43][C:36]=12.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].CN(C=O)C>C(Cl)(Cl)Cl.CC(O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[C:20]([C:35]5[CH:40]=[CH:39][N:38]=[C:37]6[NH:41][CH:42]=[CH:43][C:36]=56)=[CH:21][CH:22]=[CH:23][C:17]=4[CH:16]=3)[C:12]([F:33])=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 17749109Barium hydroxide, octahydrateHCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridineHCID 66738069HCID 66738069、化合物

生成物 1

HCID 25120565HCID 25120565、化合物収率 75%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 21906603Chloroform isopropyl alcohol溶媒

反応条件

温度
80 °C

実験手順

Combine N-(2-(1H-1,2,3-triazol-1-yl)ethyl)-5-fluoro-4-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-2-yl)pyrimidin-2-amine (0.28 g, 0.6 mmol), 4-bromo-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.51 mmol), barium hydroxide octahydrate (0.48 g, 1.52 mmol), Pd(dppf)Cl2 (40 mg, 0.05 mmol) in 4 mL of mixed solvent of DMF and water (4/1, v/v). Heat the reaction mixture to 80° C. for 45 min. Cool it to RT. Dilute with chloroform/IPA (3:1, v/v) 50 mL. Wash with water and saturated aqueous sodium chloride and dry over magnesium sulfate. Remove the organic solvent to give the crude product. Purify by column chromatography (hexane to ethyl acetate) to afford the title compound (0.17 g, 75%). MS (ES) m/z 457 [M+1]+.

後処理

  1. temperatureCool it to RT
  2. washWash with water and saturated aqueous sodium chloride
  3. dry with materialdry over magnesium sulfate
  4. customRemove the organic solvent
  5. customto give the crude product
  6. customPurify by column chromatography (hexane to ethyl acetate)

出典と根拠

ORDレコード
ord-3de2d4c64ee84fb188823c42b0cb19d7
出典データセット
uspto-grants-2012_02
特許番号
US08114872B2

反応ノート

読み込み中…