6-Bromo-3,4-dihydro-2H-isoquinolin-1-one → (4-Morpholin-4-yl-phenyl)-[5-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-carbamic acid tert-butyl ester

HRID 605919Notes

Reaction equation

HRID 605919 reaction equation
[C:1]([O:5][C:6](=[O:42])[N:7]([C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[CH:32][CH:31]=1)[C:8]1[C:9]2[N:10]([N:27]=[CH:28][N:29]=2)[C:11]([Sn](CCCC)(CCCC)CCCC)=[CH:12][N:13]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:44]1[CH:45]=[C:46]2[C:51](=[CH:52][CH:53]=1)[C:50](=[O:54])[NH:49][CH2:48][CH2:47]2>CN(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:1]([O:5][C:6](=[O:42])[N:7]([C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:37][CH2:38][O:39][CH2:40][CH2:41]2)=[CH:32][CH:31]=1)[C:8]1[C:9]2[N:10]([N:27]=[CH:28][N:29]=2)[C:11]([C:44]2[CH:45]=[C:46]3[C:51](=[CH:52][CH:53]=2)[C:50](=[O:54])[NH:49][CH2:48][CH2:47]3)=[CH:12][N:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 218654506-Bromo-3,4-dihydro-2H-isoquinolin-1-oneHCID 67047357(4-Morpholin-4-yl-phenyl)-(5-tributylstannanyl-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-carbamic acid tert-butyl ester

Product 1

HCID 67047378(4-Morpholin-4-yl-phenyl)-[5-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-carbamic acid tert-butyl esterYield 37%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a degassed solution of (4-morpholin-4-yl-phenyl)-(5-tributylstannanyl-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-carbamic acid tert-butyl ester (100 mg, 0.15 mmol) and 6-bromo-3,4-dihydro-2H-isoquinolin-1-one in DMF (1 mL) is added tetrakis(triphenylphosphine)palladium(0) (17 mg, 0.015 mmol) and the reaction mixture is stirred at 90° C. overnight. After removing the solvent in vacuo, the residue is purified by silica gel column chromatography. Elution with 1:1 petroleum ether:ethyl acetate and ethyl acetate affords the target compound as a yellow solid (30 mg, 37%).

Workup

  1. customAfter removing the solvent in vacuo
  2. customthe residue is purified by silica gel column chromatography
  3. washElution with 1:1 petroleum ether

Sources & evidence

ORD record
ord-2cda73957cda45f587e130580e0967cf
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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