Sodium Carbonate → Benzoic acid N'-[3-(4'-fluoro-biphenyl-2-yl)-propionyl]-N'-isopropyl--hydrazide

HRID 1724145

반응식

HRID 1724145 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([N:12]([CH:22]([CH3:24])[CH3:23])[NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11].C([O-])([O-])=O.[Na+].[Na+].[F:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1>COCCOC>[F:31][C:32]1[CH:37]=[CH:36][C:35]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][CH2:9][C:10]([N:12]([CH:22]([CH3:24])[CH3:23])[NH:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:11])=[CH:34][CH:33]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 57560116Benzoic acid N'-[3-(2-bromo-phenyl)-propionyl]-N'-isopropyl-hydrazide

생성물 1

HCID 57560104Benzoic acid N'-[3-(4'-fluoro-biphenyl-2-yl)-propionyl]-N'-isopropyl--hydrazide수율 79%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of benzoic acid N′-[3-(2-bromo-phenyl)-propionyl]-N′-isopropyl-hydrazide (50 mg, 0.13 mmol) in DME (4 ml)/2M Na2CO3 (225 μL, 0.45 mmol) was treated with 4-fluoro-phenylboronic acid (29 mg, 0.19 mmol) and Pd[PPh3]4 (15 mg, 0.013 mmol) for 18 hours at 90° C. The reaction mixture was partitioned between water and dichloromethane. 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 20-50% ethyl acetate/hexanes gradient to afford the product as a solid (41 mg, 79%). LC-MS m/e 405.25 (M+H+)

후처리

  1. customThe reaction mixture was partitioned between water and dichloromethane
  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 20-50% ethyl acetate/hexanes gradient

출처 및 근거

ORD 기록
ord-e7f1996252c84ec9bcad1ead4418e2ed
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07485752B2

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