Sodium Carbonate → 3-Nitro-5-phenylpicolinonitrile

HRID 69938

반응식

HRID 69938 반응식
Br[C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[N+:10]([C:4]1[C:5]([C:8]#[N:9])=[N:6][CH:7]=[C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1)([O-:12])=[O:11]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

생성물 1

HCID 463147453-Nitro-5-phenylpicolinonitrile

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

5-bromo-3-nitropicolinonitrile (1 eq) and phenylboronic acid (1.5 eq) was mixed with 15 mL of 1,4-dioxane and 5 mL of 2 M Na2CO3 aqueous solution in a glass pressure tube. The reaction mixture was degassed by anhydrous N2 stream for 5 min followed by the addition of Pd(dppf)Cl2-DCM (0.1 eq). The reaction mixture was stirred at 100° C. for 3 hours. Then the mixture was diluted with 100 mL of ethyl acetate and washed with water, brine, then dried over MgSO4, filtered, and evaporated under reduced pressure to give crude product, which was triturated by DCM, ether, hexanes to give the pure titled compound. LC/MS (m/z): 226.1 (MH+).

후처리

  1. customThe reaction mixture was degassed by anhydrous N2 stream for 5 min
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give crude product, which
  7. customwas triturated by DCM, ether, hexanes

출처 및 근거

ORD 기록
ord-d9bd29a468344207916a81149c67d060
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822497B2

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