Benzyl Bromide → 5-(4-bromophenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl ester

HRID 631932노트

반응식

HRID 631932 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.O>[CH2:22]([O:15][C:14]([C:9]1[N:10]([CH3:13])[N:11]=[N:12][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:16])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 712662515-(4-Bromophenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid

생성물 1

HCID 715003775-(4-bromophenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl ester수율 99.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 5-(4-bromophenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid (209 mg, 0.74 mmol) and sodium bicarbonate (187 mg, 2.22 mmol) in DMF (10 mL) was added an excess of benzyl bromide (380 mg, 264 μL, 2.22 mmol) at room temperature under nitrogen atmosphere. The resulting colorless reaction mixture was stirred for 15 h at which time LC/MS and TLC analysis indicated the absence of starting material. The mixture was diluted with water and extracted with ethyl acetate (2×70 mL). The combined extracts were washed with brine solution and dried over anhydrous MgSO4. Filtration and concentration gave the crude colorless oil which was purified using an ISCO (40 g) column chromatography eluting with ethyl acetate in hexanes (0-60%). The desired fractions were collected and the solvent was removed under vacuum to isolate the 5-(4-bromophenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl ester as a viscous oil (275 mg, 99% yield). LC/MS calcd. for C17H14BrN3O2 (m/e) 373, obsd. 373.8 [M+H, ES+].

후처리

  1. extractionextracted with ethyl acetate (2×70 mL)
  2. washThe combined extracts were washed with brine solution
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationFiltration and concentration
  5. customgave the crude colorless oil which
  6. customwas purified
  7. washeluting with ethyl acetate in hexanes (0-60%)
  8. customThe desired fractions were collected
  9. customthe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-2d896fcb024f4e2ca56c9de025404636
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321738B2

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