Triphenylphosphine → 1-(2-(2-Nitro-5-(piperidin-1-yl)phenyl)pyridin-4-yl)-3-phenylpropan-1-one

HRID 1408001노트

반응식

HRID 1408001 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1B1OC(C)(C)C(C)(C)O1)([O-:3])=[O:2].Br[C:26]1[CH:31]=[C:30]([C:32](=[O:41])[CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:29]=[CH:28][N:27]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C([O-])([O-])=O.[Na+].[Na+].C(COC)OC.C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)=[CH:6][C:5]=1[C:28]1[CH:29]=[C:30]([C:32](=[O:41])[CH2:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:31]=[CH:26][N:27]=1)([O-:3])=[O:2]

참가 물질

8

반응물 3

HCID 11776TriphenylphosphineHCID 66587487HCID 66587487, 화합물HCID 867059361-(2-Bromopyridin-4-yl)-3-phenylpropan-1-one

생성물 1

HCID 675181571-(2-(2-Nitro-5-(piperidin-1-yl)phenyl)pyridin-4-yl)-3-phenylpropan-1-one수율 81.5%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매HCID 10340Sodium Carbonate용매

실험 절차

A solution of 200 mg of 1-(4-nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine 1.1e, 168 mg of 1-(2-bromopyridin-4-yl)-3-phenylpropan-1-one 5.1a, 12 mg of Pd(OAc)2, 58 mg of PPh3 in 1.25 mL of 2 N aqueous Na2CO3 solution and 3 mL of dimethoxyethane was refluxed for 4 h. The mixture was diluted with ethyl acetate and washed with water twice. The combined organic layer was dried over Na2SO4 and the solvent was evaporated. The residue was chromatographed on silica gel eluting with a gradient of 0% to 7% ethyl acetate in dichloromethane to give 196 mg of product.

후처리

  1. washwashed with water twice
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. customthe solvent was evaporated
  4. customThe residue was chromatographed on silica gel eluting with a gradient of 0% to 7% ethyl acetate in dichloromethane

출처 및 근거

ORD 기록
ord-bd6a3b6191084252bbde660ea77d52c7
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916569B2

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