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Water → 9-(1-bromoethyl)-8-fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene

HRID 1530731
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HRID 1530731 반응식
P(Br)(Br)[Br:2].[F:5][C:6]1[C:28]([CH:29](O)[CH3:30])=[CH:27][C:9]2[C:10]3[N:14]([CH2:15][CH2:16][O:17][C:8]=2[CH:7]=1)[CH:13]=[C:12]([C:18]1[N:19]([CH:24]([CH3:26])[CH3:25])[N:20]=[C:21]([CH3:23])[N:22]=1)[N:11]=3.O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:2][CH:29]([C:28]1[C:6]([F:5])=[CH:7][C:8]2[O:17][CH2:16][CH2:15][N:14]3[C:10](=[N:11][C:12]([C:18]4[N:19]([CH:24]([CH3:26])[CH3:25])[N:20]=[C:21]([CH3:23])[N:22]=4)=[CH:13]3)[C:9]=2[CH:27]=1)[CH3:30]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 683128551-[8-Fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-yl]ethanol

생성물 1

HCID 683131309-(1-bromoethyl)-8-fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene수율 88%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Phosphorus tribromide (0.53 mL of a 1.0 M solution in DCM) was added to a solution of 1-[8-fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-yl]ethanol (98 mg, 0.26 mmol) in DCM (1 mL) at 0° C. The mixture was warmed to RT and stirred for 20 h. Water (2 mL) and sat. NaHCO3 (2 mL) were added and the mixture was extracted with DCM. The combined organics were washed (brine), dried (Na2SO4) and concentrated in vacuo to give the title compound (100 mg, 0.23 mmol, 88%) as a pale yellow solid. The product was taken on without further purification. 1H NMR (CDCl3, 300 MHz): δ 8.72 (1H, d, J=8.7 Hz), 7.60 (1H, s), 6.75 (1H, d, J=11.0 Hz), 5.82 (1H, sept., J=6.6 Hz), 5.45 (1H, q, J=7.0 Hz), 4.52-4.49 (2H, m), 4.44-4.41 (2H, m), 2.42 (3H, s), 2.11 (3H, d, J=7.0 Hz), 1.60 (6H, d, J=6.6 Hz)

후처리

  1. extractionthe mixture was extracted with DCM
  2. washThe combined organics were washed (brine)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2cbb9fc1763d4dcd8e4761afda20e42e
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090628B2

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