Tetrahydrofuran → HCID 90093834, compound

HRID 927265Notes

Reaction equation

C1CCN2C(=NCCC2)CC1.[CH2:12]([N:19]1[C:28]([CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24](Br)[CH:25]=2)[C:20]1=[O:38])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[F:39][C:40]1[CH:45]=[CH:44][C:43]([C@H:46]([NH2:48])[CH3:47])=[CH:42][CH:41]=1.C1C[O:52][CH2:51]C1>CC([O-])=O.CC([O-])=O.[Pd+2].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[CH2:12]([N:19]1[C:28]([CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:51](=[O:52])[NH:48][C@@H:46]([C:43]3[CH:44]=[CH:45][C:40]([F:39])=[CH:41][CH:42]=3)[CH3:47])[CH:25]=2)[C:20]1=[O:38])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 150 °C

Procedure

DBU (4.50 equiv.) was added to a stirred, capped mixture of methyl 5-(2-benzyl-6-bromo-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (1 eq), Pd(OAc)2 (0.05 equiv.), molybdenum hexacarbonyl (1.0 equiv.) and (R)-1-(4-fluorophenyl)ethylamine (1.20 equiv.) in THF (0.2 M) and the mixture was stirred at 150° C. for 30 min. in a microwave. The mixture was purified by preparative TLC [1 mm] eluting with 50% EtOAc/hexanes to afford (R)-methyl 5-(2-benzyl-6-((1-(4-fluorophenyl)ethyl)carbamoyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate.

Workup

customcapped
customThe mixture was purified by preparative TLC [1 mm]
washeluting with 50% EtOAc/hexanes

Sources & evidence

ORD record: ord-99a6ad020f6f49c78a3871132b6d01a9
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290454B2

Reaction notes

Loading…