Nitrogen → tert-butyl 4-[(6-cyano-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate

HRID 2173287노트

반응식

HRID 2173287 반응식
Br[C:2]1[C:3]([O:26][CH3:27])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)[O:7][CH2:6][CH2:5]2.N#N.[CH3:30][N:31](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[C-]#N.[Zn+2]>[C:30]([C:2]1[C:3]([O:26][CH3:27])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:15][CH2:14]1)[O:7][CH2:6][CH2:5]2)#[N:31]

참가 물질

6

반응물 3

HCID 947NitrogenHCID 6228DimethylformamideHCID 68433391tert-butyl 4-[(6-bromo-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate

생성물 1

HCID 67517697tert-butyl 4-[(6-cyano-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

실험 절차

To a solution of tert-butyl 4-[(6-bromo-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate (50 mg, 0.11 mmol), Pd(PPh3)4 (20 mg) and Zn(CN)2 (26 mg, 0.23 mmol) in 5 mL of anhydrous DMF was to 110° C. at N2 atmosphere overnight. The reaction was cooled to room temperature, extracted by EtOAc, washed by water then by brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified with prep-TLC to afford tert-butyl 4-[(6-cyano-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate.

후처리

  1. extractionextracted by EtOAc
  2. washwashed by water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified with prep-TLC

출처 및 근거

ORD 기록
ord-89986f29258e4ca5b6deff20df97e613
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056859B2

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