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

HRID 625259ノート

反応式

HRID 625259 の反応式
[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]

参加物

8

反応物 3

HCID 11776TriphenylphosphineHCID 66587487HCID 66587487、化合物HCID 867059361-(2-Bromopyridin-4-yl)-3-phenylpropan-1-one

生成物 1

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

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒HCID 10340Sodium Carbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-71b72c41d58d4ed28fd3e96060d23a08
出典データセット
uspto-grants-2016_04
特許番号
US09301951B2

反応ノート

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