Hydrochloric Acid → 3-Amino-1-phenyl-1H-pyrazole-4-carbonitrile

HRID 1961507

반응식

HRID 1961507 반응식
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[CH:5][NH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.[CH2:25](Cl)Cl>C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[NH:1]([C:2]1[C:6]([C:7]#[N:8])=[CH:5][N:4]([C:19]2[CH:25]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:3]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6344DichloromethaneHCID 66827Phenylboronic AcidHCID 178510443HCID 178510443, 화합물

생성물 2

HCID 27742493-Amino-1-phenyl-1H-pyrazole-4-carbonitrileHCID 672543033-anilino-1-phenyl-1H-pyrazole-4-carbonitrile

시약·촉매·용매 1

HCID 8895Cupric acetate촉매

실험 절차

3-amino-1H-pyrazole-4-carbonitrile (200 mg, 1.850 mmol), copper(II) acetate (504 mg, 2.78 mmol), phenylboronic acid (451 mg, 3.70 mmol) and pyridine (0.599 mL, 7.40 mmol) were stirred in DCM (20 mL) at room temperature overnight. 2 N HCl was added and the products extracted in EtOAc (×2). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by MPLC (2-30% EtOAc-hexanes) gave 3-anilino-1-phenyl-1H-pyrazole-4-carbonitrile (A) as a yellow solid and 3-amino-1-phenyl-1H-pyrazole-4-carbonitrile (B) as a pale yellow solid. 5-amino-1-phenyl-1H-pyrazole-4-carbonitrile was also isolated.

후처리

  1. extractionthe products extracted in EtOAc (×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by MPLC (2-30% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-373c8816e2fb4293a7ec3800604d42b7
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415346B2

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