tert-Butyl piperazine-1-carboxylate → tert-Butyl 4-(isoquinolin-5-yl)piperazine-1-carboxylate

HRID 459830노트

반응식

HRID 459830 반응식
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:58]([O:62][C:63]([N:65]1[CH2:70][CH2:69][NH:68][CH2:67][CH2:66]1)=[O:64])([CH3:61])([CH3:60])[CH3:59].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:58]([O:62][C:63]([N:65]1[CH2:70][CH2:69][N:68]([C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][N:6]=[CH:7]3)[CH2:67][CH2:66]1)=[O:64])([CH3:61])([CH3:59])[CH3:60]

참가 물질

8

반응물 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 7364875-BromoisoquinolineHCID 23676156Sodium t-butoxide

생성물 1

HCID 21070949tert-Butyl 4-(isoquinolin-5-yl)piperazine-1-carboxylate

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

5-Bromoisoquinoline (1.37 g) from Step 1 was dissolved in 10 mL of toluene. To this solution was added palladium acetate (74 mg), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (205 mg), 1-(tert-butoxycarbonyl)piperazine (1.29 g) and sodium tert-butoxide (885 mg). This reaction mixture was heated to 100° C. for 8 hours and then allowed to cool to room temperature. The cooled reaction mix was diluted with ethyl acetate (EtOAc) and washed with water, and the organic layer was separated, dried over magnesium sulfate (MgSO4), and concentrated in vacuo. The resulting residue was chromatographed to yield 4-isoquinoline-5-yl-piperazine-1-carboxylic acid tert-butyl ester as 1.5 g of a white solid.

후처리

  1. temperatureto cool to room temperature
  2. customThe cooled reaction
  3. additionmix
  4. washwashed with water
  5. customthe organic layer was separated
  6. dry with materialdried over magnesium sulfate (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was chromatographed

출처 및 근거

ORD 기록
ord-61939400dbce484b9a70d39c46e1a9e2
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196088B2

반응 노트

불러오는 중…