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

HRID 1408003노트

반응식

HRID 1408003 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].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]

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27629942-Chloro-4-pyridinecarboxaldehydeHCID 665874871-[4-Nitro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-piperidine

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-0ad3158d179d4eea842a88fa5574ca90
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916569B2

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