Sodium Carbonate → 2-(2-Nitro-5-(piperidin-1-yl)phenyl)isonicotinaldehyde

HRID 625261ノート

反応式

HRID 625261 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].Cl[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][N:33]=1)[CH:29]=[O:30].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].COCCOC>[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:26]1[CH:27]=[C:28]([CH:31]=[CH:32][N:33]=1)[CH:29]=[O:30])([O-:3])=[O:2]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27629942-Chloro-4-pyridinecarboxaldehydeHCID 66587487HCID 66587487、化合物

生成物 1

HCID 867059382-(2-Nitro-5-(piperidin-1-yl)phenyl)isonicotinaldehyde

試薬・触媒・溶媒 3

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

実験手順

A mixture of 200 mg of 1-(4-nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine 1e, 85 mg of 2-chloroisonicotinaldehyde, 6.7 mg of Pd(OAc)2, 31 mg of PPh3, 1.25 mL of 2 N aqueous Na2CO3 solution, and 3 mL of DME were refluxed 2 h. The mixture was diluted with ethyl acetate and washed 3× with water. The organic extracts were washed with brine and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silica gel eluting with 10% ethyl acetate in dichloromethane. This gave 114 mg of product. MS (ES, m/z): 312.0 [M+H]+.

後処理

  1. temperaturewere refluxed 2 h
  2. washwashed 3× with water
  3. washThe organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe residue was chromatographed on silica gel eluting with 10% ethyl acetate in dichloromethane

出典と根拠

ORDレコード
ord-88a2c4ad37664872a3af4ee9ffecdf5c
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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