Potassium Carbonate → 6-Bromo-3-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-[1,2,4]-triazolo[4,3-a]pyridine

HRID 1041903노트

반응식

HRID 1041903 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=3)=[N:9][N:10]=2)[CH:7]=1.Cl.Br[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:12]=3)=[N:9][N:10]=2)[CH:7]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 129555404-(2-Bromoethyl)morpholine hydrochlorideHCID 669777183-(6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)phenol

생성물 1

HCID 669775836-Bromo-3-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-[1,2,4]-triazolo[4,3-a]pyridine수율 98%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of Example 10 step a (250 mg, 1.21 mmol), N-(2-bromoethyl)morpholine hydrochloride (306 mg, 1.32 mmol) and K2CO3 (500 mg, 3.62 mmol) in DMF (20 mL) was heated at 50° C. for 24 h. The reaction was then allowed to cool to RT and concentrated in vacuo. The residue was purified by FCC (DCM:MeOH, 1:0 to 9:1) to afford the title compound (479 mg, 98%) as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 8.44 (1 H, dd, J 1.7, 1), 7.74-7.69 (1 H, m), 7.50 (1 H, t, J 7.9), 7.39-7.35 (2 H, m), 7.35-7.30 (1 H, m), 7.14-7.08 (1 H, m), 4.21 (2 H, t, J 5.6), 3.74 (4 H, t, J 4.6), 2.85 (2 H, t, J 5.6), 2.63-2.56 (4 H, m).

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by FCC (DCM:MeOH, 1:0 to 9:1)

출처 및 근거

ORD 기록
ord-e82fa9190dbc4272a5485489d96209ee
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557797B2

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