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

HRID 2427542ノート

反応式

HRID 2427542 の反応式
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

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 5718464-(Trifluoromethoxy)benzylamineHCID 59512232HCID 59512232、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c8891f0104c14584ad0b668e5f99363b
出典データセット
uspto-grants-2011_06
特許番号
US07968570B2

反応ノート

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