Sodium Carbonate → benzoic acid N'-[2-(4'-fluoro-biphenyl-2-ylsulfanyl)-acetyl]-N'-isopropyl-hydrazide

HRID 2250942노트

반응식

HRID 2250942 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+].[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[S: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 58689908benzoic acid N'-[2-(2-bromo-phenylsulfanyl)-acetyl]-N'-isopropyl-hydrazide

생성물 1

HCID 11553583benzoic acid N'-[2-(4'-fluoro-biphenyl-2-ylsulfanyl)-acetyl]-N'-isopropyl-hydrazide수율 20%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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 4-fluorophenylboronic acid (35 mg, 0.25 mmol) and Pd[PPh3]4 (14 mg, 0.012 mmol) for 12 hours at 90° C. 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 (9.5 mg, 20%). MS m/e 423.22 (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-91ea0f14f831467aa2d2cd6e06986dab
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07317125B2

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