Potassium Carbonate → Bromo-7-methoxy-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one

HRID 2427542노트

반응식

HRID 2427542 반응식
CO[C:3](=[O:14])[C:4]1[C:9](C)=[CH:8][C:7](Br)=[CH:6][C:5]=1[CH2:12][Br:13].[F:15][C:16]([F:27])([F:26])[O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.[C:28]([O-])([O-])=[O:29].[K+].[K+]>C1(C)C=CC=CC=1>[Br:13][CH:12]1[C:5]2[C:4](=[C:9]([O:29][CH3:28])[CH:8]=[CH:7][CH:6]=2)[C:3](=[O:14])[N:23]1[CH2:22][C:21]1[CH:24]=[CH:25][C:18]([O:17][C:16]([F:26])([F:27])[F:15])=[CH:19][CH:20]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 5718464-(Trifluoromethoxy)benzylamineHCID 59512232HCID 59512232, 화합물

생성물 1

HCID 67250179Bromo-7-methoxy-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one수율 66%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

4-Bromo-2-bromomethyl-6-methylbenzoic acid methyl ester (762 mg, 2.37 mmol), 4-trifluoromethoxy benzylamine (0.543 mL, 3.56 mmol) and K2CO3 (981 mg, 7.10 mmol) were stirred in toluene (10 mL) at 95° C. for 12 hours. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the product was purified by column chromatography (10-25% EtOAc/Hexanes) to afford a yellow oil (650 mg, 66%). 1H NMR (300 MHz, CDCl3): δ 7.33-7.36 (m, 2H), 7.18 (d, 2H), 7.13 (s, 1H), 7.07 (s, 1H), 4.75 (s, 2H), 4.22 (s, 2H), 4.00 (s, 3H).

후처리

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe product was purified by column chromatography (10-25% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-c8891f0104c14584ad0b668e5f99363b
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968570B2

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