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

HRID 1371516ノート

反応式

HRID 1371516 の反応式
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]

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 98591348-Bromoisoquinoline

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
90 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-d00ee3b12e2e4e569ffb7cb9d556b86b
出典データセット
uspto-grants-2007_01
特許番号
US07157463B2

反応ノート

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