Bromine → 2-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol

HRID 891842노트

반응식

HRID 891842 반응식
[N:1]1[N:2]2[CH:13]=[CH:12][N:11]=[C:3]2[N:4]=[C:5]([C:7]([OH:10])([CH3:9])[CH3:8])[CH:6]=1.C([O-])(=O)C.[Na+].[Br:19]Br>C(O)(=O)C>[Br:19][C:13]1[N:2]2[N:1]=[CH:6][C:5]([C:7]([OH:10])([CH3:9])[CH3:8])=[N:4][C:3]2=[N:11][CH:12]=1

참가 물질

5

반응물 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 11218170HCID 11218170, 화합물

생성물 1

HCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol수율 77.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

To a stirred solution of 2-(imidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol (5.55 g, 31.1 mmol) in acetic acid (100 ml) was added sodium acetate (3.83 g, 46.7 mmol), then, dropwise over 5 min, a solution of bromine (1.77 ml, 34.4 mmol) in acetic acid (12 ml). The solution was stirred at room temperature for 25 min, then partitioned between saturated aqueous NaHCO3 (2 l) and ethyl acetate (1 l). The aqueous layer (pH 7) was further extracted with ethyl acetate (1 l), and the combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 2% MeOH/CH2Cl2) to afford 6.17 g (77%) of the title compound as a yellow solid: 1H NMR (360 MHz, CDCl3) δ 1.70 (6H, s), 3.12 (1H, br s), 7.95 (1H, s), 8.80 (1H, s).

후처리

  1. custompartitioned between saturated aqueous NaHCO3 (2 l) and ethyl acetate (1 l)
  2. extractionThe aqueous layer (pH 7) was further extracted with ethyl acetate (1 l)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (silica gel, 2% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-51d3a0cb91754e87bde4c57857442d8d
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005431B2

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