Water → HCID 59408872, compound

HRID 1423369Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[C:12]1[CH:11]=[CH:10][C:9]([C:18]#[N:19])=[CH:8][C:7]=1[NH:6][C:5]2=[O:20].BrC1C=CC(S(O[C@@H:32]2[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:34]([C:44]([O:46][CH3:47])=[O:45])[CH2:33]2)(=O)=O)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN1C(=O)CCC1.CCOC(C)=O>[Br:1][C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:13]2[C:4](=[C:5]([O:20][C@H:32]3[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:34]([C:44]([O:46][CH3:47])=[O:45])[CH2:33]3)[N:6]=[C:7]3[C:12]=2[CH:11]=[CH:10][C:9]([C:18]#[N:19])=[CH:8]3)[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 8-bromo-9-methoxy-6-oxo-5,6-dihydrophenanthridine-3-carbonitrile (C1), 8-bromo-9-methoxy-6-oxo-5,6-dihydrophenanthridine-3-carbonitrile (354 mg, 1.07 mmol) in NMP (10 mL) was added 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (549 mg, 1.18 mmol) and Cs2CO3 (876 mg, 2.69 mmol). The mixture was then heated to 60° C. for 18 h, and worked up with water and EtOAc. The organic layer was washed with brine, dried over MgSO4, and the solvent was removed in vacuo. The crude material was purified on silica (gradient elution, 10-50% EtOAc/hex) to yield the title compound. LRMS ((M-Boc)+H)+=456.2.

Workup

washThe organic layer was washed with brine
dry with materialdried over MgSO4
customthe solvent was removed in vacuo
customThe crude material was purified on silica (gradient elution, 10-50% EtOAc/hex)

Sources & evidence

ORD record: ord-19f39a667e26442c936290a06fd06a26
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927569B2

Reaction notes

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