1-Bromo-2-methylpropane → 2-((4-chlorophenoxy)methyl)-1-isobutyl-1H-benzo[d]imidazole

HRID 537300

반응식

HRID 537300 반응식
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].[CH3:25][CH:26]([CH3:29])[CH2:27]Br>CN(C=O)C>[CH3:25][CH:26]([CH3:29])[CH2:27][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 3939882-[(4-chlorophenoxy)methyl]-1H-1,3-benzodiazole

생성물 1

HCID 7121812-((4-chlorophenoxy)methyl)-1-isobutyl-1H-benzo[d]imidazole수율 95.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 52 (5.17 g, 0.02 mol) in DMF (50 mL) was added K2CO3 (5.53 g, 0.04 mol) followed by addition of 2-methylpropyl bromide (5.2 g, 0.038 mol) under Ar. The resulting mixture was stirred at rt for 48 hr. HPLC analysis showed that the reaction was not complete. The reaction mixture was further heated at 90° C. for 8 hr, at which point HPLC analysis showed the reaction was complete. The reaction mixture was cooled to rt and filtered. The filter cake was washed with EtOAc (100 mL). The filtrate was washed with H2O (2×75 mL) and brine (100 mL), filtered through phase separation filter paper, and concentrated in vacuo to give an oil (6 g) which solidified. The solid was triturated with hexanes (50 mL), filtered, washed with hexanes (25 mL), and dried to give 4.25 g (80%) of Compound #4. HPLC analysis showed a purity of 100%. 1H NMR (300 MHz, CDCl3): δ 7.85 (m, 1H), 7.45-7.25 (m, 5H), 7.05 (m. 2H), 5.4 (s, 2H), 4.1 (d, 2H), 2.35 (m, 1H), 1.0 (d, 6H) ppm.

후처리

  1. temperatureThe reaction mixture was further heated at 90° C. for 8 hr, at which point HPLC analysis
  2. temperatureThe reaction mixture was cooled to rt
  3. filtrationfiltered
  4. washThe filter cake was washed with EtOAc (100 mL)
  5. washThe filtrate was washed with H2O (2×75 mL) and brine (100 mL)
  6. filtrationfiltered through phase separation
  7. filtrationfilter paper
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-68369db91f7849c48785a171cbb2fa90
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859780B2

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