Sodium Carbonate → benzoic acid N'-[2-(2',3'-dimethyl-5-fluoro-biphenyl-2-yloxy)-acetyl]-N'-isopropyl-hydrazide

HRID 2250914

反応式

HRID 2250914 の反応式
Br[C:2]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:3]=1[O:4][CH2:5][C:6]([N:8]([CH:18]([CH3:20])[CH3:19])[NH:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7].C([O-])([O-])=O.[Na+].[Na+].[CH3:32][C:33]1[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=1B(O)O>COCCOC>[CH3:32][C:33]1[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=1[C:2]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:3]=1[O:4][CH2:5][C:6]([N:8]([CH:18]([CH3:20])[CH3:19])[NH:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 27733952,3-Dimethylphenylboronic acidHCID 58689907benzoic acid N'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide

生成物 1

HCID 11618926benzoic acid N'-[2-(2',3'-dimethyl-5-fluoro-biphenyl-2-yloxy)-acetyl]-N'-isopropyl-hydrazide収率 57%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

A solution of benzoic acid N′-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N′-isopropyl-hydrazide (50 mg, 0.122 mmol) in DME (3 ml)/2M Na2CO3 (0.215 ml, 0.427 mmol) was treated with 2,3-dimethylphenylboronic acid (27 mg, 0.183 mmol) and Pd[PPh3]4 (28 mg, 0.0244 mmol) for 12 hours at 90° C. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 20-30% ethyl acetate/hexanes gradient to afford the product as a white solid (30 mg, 57%). MS m/e 435.30 (M+H+)

後処理

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with a 20-30% ethyl acetate/hexanes gradient

出典と根拠

ORDレコード
ord-74809c6cc32e416b84434d771ec3c91d
出典データセット
uspto-grants-2008_01
特許番号
US07317125B2

関連ノート

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