Potassium Carbonate → HCID 68690442, compound

HRID 1159115Notes

Reaction equation

[CH2:1]([N:8]1[CH2:23][CH2:22][N:11]2[C:12](=[O:21])[C:13]3[CH:14]=[CH:15][C:16](Br)=[CH:17][C:18]=3[CH2:19][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24](N1CCN2C(=O)C3C(Br)=CC=CC=3C[C@@H]2C1)[C:25]1C=CC=C[CH:26]=1.C(B(O)O)(C)=C.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.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>[CH2:1]([N:8]1[CH2:23][CH2:22][N:11]2[C:12](=[O:21])[C:13]3[CH:14]=[CH:15][C:16]([C:25]([CH3:26])=[CH2:24])=[CH:17][C:18]=3[CH2:19][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A degassed mixture of (R)-2-benzyl-9-bromo-1,2,3,4,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-6-one with (R)-2-benzyl-7-bromo-1,2,3,4,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-6-one (9-Br:7-Br=1:2, 100 mg, 0.27 mmol), isopropenyl boronic acid (46 mg, 0.54 mmol), tetrakis(triphenylphosphine)palladium (16 mg, 0.013 mmol) and K2CO3 (82 mg, 0.59 mmol) in DME (2 mL) and water (0.6 mL) was heated at 80° C. for 9 h to give dark brownish reaction mixture. The mixture was then cooled, quenched with 10 mL of water, extracted with ethyl acetate (3×10 mL), dried over MgSO4, and concentrated in vacuo to give the desired product as brown oil (No 7-isomeric product was observed).

Workup

customto give dark
custombrownish reaction mixture
temperatureThe mixture was then cooled
customquenched with 10 mL of water
extractionextracted with ethyl acetate (3×10 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6b5eee272a6147a98e9c626076c5f85c
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812024B2

Reaction notes

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