Dimethylformamide → HCID 25120565, 화합물

HRID 1640928노트

반응식

HRID 1640928 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 25120565HCID 25120565, 화합물수율 75%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 21906603Chloroform isopropyl alcohol용매

반응 조건

온도
80 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-3de2d4c64ee84fb188823c42b0cb19d7
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114872B2

반응 노트

불러오는 중…