Dimethylformamide → 8-(1-t-Butyloxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)isoquinoline

HRID 1371516노트

반응식

HRID 1371516 반응식
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2.[C:12](=[O:15])([O-])[O-:13].[K+].[K+].[CH3:18][N:19]([CH:21]=O)C>C(Cl)Cl.[CH-]1C=C(P(C2C=CC=CC=2)C2C=CC=CC=2)C=C1.[CH-]1C=C(P(C2C=CC=CC=2)C2C=CC=CC=2)C=C1.Cl[Pd]Cl.[Fe+2]>[C:6]([O:13][C:12]([N:19]1[CH2:21][CH2:4][C:3]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[CH:10]=[N:9][CH:8]=[CH:7]3)=[CH:2][CH2:18]1)=[O:15])([CH3:11])([CH3:7])[CH3:5]

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 98591348-Bromoisoquinoline

생성물 1

HCID 210709528-(1-t-Butyloxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)isoquinoline수율 73%

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6344Dichloromethane용매

반응 조건

온도
90 °C

실험 절차

8-Bromoisoquinoline (300 mg, 1.44 mmol) is dissolved in DMF (8.7 mL). To the solution is added Boc-piperidine boronic ester (405 mg, 1.31 mmol), dichloro(1,1′-bis(diphenylphosphino)ferrocene)palladium (II) dichloromethane adduct (58 mg, 0.079 mmol) and potassium carbonate (544 mg, 3.93 mmol). The mixture is heated to about 90° C. overnight and cooled, which is then diluted with DCM and filtered through celite. The filtrate is concentrated under vacuum to remove DCM and partitioned between EtOAc (100 mL), hexanes (100 mL) and water (100 mL). The organic fraction is concentrated and chromatographed on silica gel to give about 298 mg of 8-(1-t-butyloxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)isoquinoline (73%). EIS-MS 311.2 M+1

후처리

  1. temperaturecooled
  2. filtrationfiltered through celite
  3. concentrationThe filtrate is concentrated under vacuum
  4. customto remove DCM
  5. custompartitioned between EtOAc (100 mL), hexanes (100 mL) and water (100 mL)
  6. concentrationThe organic fraction is concentrated
  7. customchromatographed on silica gel

출처 및 근거

ORD 기록
ord-d00ee3b12e2e4e569ffb7cb9d556b86b
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157463B2

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