Sodium Carbonate → Ethyl {2-[4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenoxy]-1H-benzimidazol-1-yl}acetate

HRID 573318노트

반응식

HRID 573318 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:30]=[CH:29][C:12]([O:13][C:14]3[N:18]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:17]4[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=4[N:15]=3)=[CH:11][CH:10]=2)O1.Br[C:33]1[C:37]2=[N:38][CH:39]=[CH:40][CH:41]=[C:36]2[N:35]([CH2:42][CH3:43])[N:34]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:42]([N:35]1[C:36]2[C:37](=[N:38][CH:39]=[CH:40][CH:41]=2)[C:33]([C:9]2[CH:30]=[CH:29][C:12]([O:13][C:14]3[N:18]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:17]4[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=4[N:15]=3)=[CH:11][CH:10]=2)=[N:34]1)[CH3:43]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 667278823-bromo-1-ethyl-1H-pyrazolo[4,3-b]pyridineHCID 86688977Ethyl {2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1H-benzimidazol-1-yl}acetate

생성물 1

HCID 66727897Ethyl {2-[4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenoxy]-1H-benzimidazol-1-yl}acetate수율 18.6%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of ethyl {2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1H-benzimidazol-1-yl}acetate (540 mg), 3-bromo-1-ethyl-1H-pyrazolo[4,3-b]pyridine (289 mg), Pd(PPh3)4 (44.3 mg), Na2CO3 (474 mg) in DME (10 mL) and water (2 ml) was refluxed overnight under Ar atmosphere. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (105 mg).

후처리

  1. temperaturewas refluxed overnight under Ar atmosphere
  2. extractionextracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

출처 및 근거

ORD 기록
ord-9639a029461e40bd82144da974fdc9ab
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029536B2

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