Sodium Hydroxide → HCID 178480264、化合物

HRID 2064495ノート

反応式

HRID 2064495 の反応式
[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][CH:12]2[CH2:14][CH2:13]2)[C:7](=[NH:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[Br:18][C:19]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:20]=1[C:21](Cl)=[O:22]>O1CCCC1.O.C(OCC)(=O)C>[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][CH:12]2[CH2:13][CH2:14]2)/[C:7](=[N:15]/[C:21](=[O:22])[C:20]2[CH:24]=[C:25]([C:28]([F:29])([F:30])[F:31])[CH:26]=[CH:27][C:19]=2[Br:18])/[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 59865659HCID 59865659、化合物HCID 790215092-Bromo-5-(trifluoromethyl)benzoyl chloride

生成物 1

HCID 178480264HCID 178480264、化合物収率 93%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of Example 3E (3.52 g, 17 mmol) in tetrahydrofuran (20 mL) was added sodium hydroxide (2.72 g, 68 mmol) in water (5.00 mL), followed by addition of a solution of 2-bromo-5-(trifluoromethyl)benzoyl chloride (3.85 g, 17 mmol) in tetrahydrofuran (5 mL) dropwise at 0° C. The mixture was stirred at room temperature for 1 hour then diluted with water (20 mL) and ethyl acetate (30 mL). The layers were separated and the organic extract was washed with brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, eluted with a gradient of 15-100% hexane in solvent B, solvent B: 10:1:0.5 ethyl acetate:methanol:triethylamine) to afford the title compound (6.3 g, 93%). 1H NMR (300 MHz, DMSO-D6) δ ppm 0.41-0.52 (m, 4H) 1.13-1.27 (m, 1H) 1.40 (s, 9H) 3.94 (s, 3H) 4.20 (d, J=6.74 Hz, 2H) 6.83 (s, 1H) 7.54 (dd, J=8.53, 2.18 Hz, 1H) 7.77-7.82 (m, 2H); MS (ESI) m/z 458 [M+H]+.

後処理

  1. customThe layers were separated
  2. extractionthe organic extract
  3. washwas washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography
  8. washeluted with a gradient of 15-100% hexane in solvent B, solvent B

出典と根拠

ORDレコード
ord-c44fba441eb1495e93fa8de96eafeb4c
出典データセット
uspto-grants-2012_10
特許番号
US08288428B2

反応ノート

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