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Sodium Carbonate → benzoic acid N'-[2-(biphenyl-2-ylsulfanyl)-acetyl]-N'-isopropyl-hydrazide

HRID 2250947
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HRID 2250947 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S: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+].[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>COCCOC>[C:2]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S: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]
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참가 물질

5

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HCID 10340Sodium Carbonate2회HCID 66827Phenylboronic AcidHCID 58689908benzoic acid N'-[2-(2-bromo-phenylsulfanyl)-acetyl]-N'-isopropyl-hydrazide

생성물 1

HCID 11654322benzoic acid N'-[2-(biphenyl-2-ylsulfanyl)-acetyl]-N'-isopropyl-hydrazide수율 15%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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온도
90 °C

실험 절차

A solution of benzoic acid N′-[2-(2-bromo-phenylsulfanyl)-acetyl]-N′-isopropyl-hydrazide (50 mg, 0.123 mmol) in DME (4 ml)/2M Na2CO3 (0.215 ml, 0.43 mmoles) was treated with phenylboronic acid (30 mg, 0.25 mmol) and Pd[PPh3]4 (14 mg, 0.012 mmol) for 12 hours at 90° C. Additional amounts of Pd[PPh3]4 (28 mg, 0.025 mmol) and 2M Na2CO3 (0.215 ml, 0.43 mmoles) were added and the mixture was stirred at 90° C. for another night. The reaction mixture was partitioned between water and DCM. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was adsorbed on silica and purified on a silica gel column with a 20-50% ethyl acetate/hexane gradient. Further purification by RP HPLC afforded the product (7.2 mg, 15%). MS m/e 405.26 (M+H+)

후처리

  1. customThe reaction mixture was partitioned between water and DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on a silica gel column with a 20-50% ethyl acetate/hexane gradient
  7. customFurther purification by RP HPLC

출처 및 근거

ORD 기록
ord-51e6609854be42c4b5b15bac4f57d475
출처 데이터셋
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07317125B2

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