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N-methyl-2-pyrrolidone → HCID 71272391, 화합물

HRID 475255
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HRID 475255 반응식
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1.[CH3:17][N:18]1C(=O)CCC1>[C-]#N.[C-]#N.[Zn+2]>[O:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]1[N:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:2]([C:17]#[N:18])[C:3]=2[CH:4]=[N:5]1
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참가 물질

4

반응물 2

HCID 13387N-methyl-2-pyrrolidoneHCID 574747294-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

생성물 1

HCID 71272391HCID 71272391, 화합물수율 75%

시약·촉매·용매 1

HCID 11186Zinc cyanide (Zn(CN)2)촉매

반응 조건

온도
85 °C

실험 절차

To a mixture of 196 (0.57 g, 2.05 mmol), Zn(CN)2 (264 mg, 2.25 mmol) in NMP (6 mL) under an argon atmosphere was added (Ph3P)4Pd(0) (356 mg, 0.31 mmol). The mixture was heated at 85° C. overnight, cooled, and partitioned between EtOAc (300 mL) and H2O (50 mL). The organic layer was separated and washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with 1% MeOH/DCM to afford 430 mg (75%) of 1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile (198) as yellow solid: MS (ESI) m/z=228 [M+1]+.

후처리

  1. temperaturecooled
  2. custompartitioned between EtOAc (300 mL) and H2O (50 mL)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by SiO2 chromatography
  8. washeluting with 1% MeOH/DCM

출처 및 근거

ORD 기록
ord-73434ecbd7534df385ada9867b319574
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08637537B2

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