Triphenylphosphine → HCID 59645483, compound

HRID 2253307Notes

Reaction equation

CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Br:15][C:16]1[C:25]2[N:26]=[C:27]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[C:31]([N+:36]([O-:38])=[O:37])[CH:30]=3)[NH:28][C:24]=2[C:23]2[C:22](=[O:39])[NH:21][C:20](=[O:40])[C:19]([CH3:42])([CH3:41])[C:18]=2[CH:17]=1.[CH3:43][O:44][C:45]1[CH:46]=[C:47]([CH2:53][CH2:54][N:55]([CH2:63][CH2:64][CH2:65]O)[C:56](=[O:62])[O:57][C:58]([CH3:61])([CH3:60])[CH3:59])[CH:48]=[CH:49][C:50]=1[O:51][CH3:52].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.C(Cl)Cl.CC(C)=O>[Br:15][C:16]1[C:25]2[N:26]=[C:27]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[C:31]([N+:36]([O-:38])=[O:37])[CH:30]=3)[NH:28][C:24]=2[C:23]2[C:22](=[O:39])[N:21]([CH2:65][CH2:64][CH2:63][N:55]([CH2:54][CH2:53][C:47]3[CH:48]=[CH:49][C:50]([O:51][CH3:52])=[C:45]([O:44][CH3:43])[CH:46]=3)[C:56](=[O:62])[O:57][C:58]([CH3:60])([CH3:61])[CH3:59])[C:20](=[O:40])[C:19]([CH3:42])([CH3:41])[C:18]=2[CH:17]=1

Participants

Conditions

Temperature: 25 °C

Procedure

DIAD (1.15 mL, 5.87 mmol) was added dropwise to a solution of 4-bromo-6,6-dimethyl-2-(4-methyl-3-nitrophenyl)-1H-imidazo[4,5-h]isoquinoline-7,9(6H,8H)-dione (1.3 g, 2.93 mmol), tert-butyl [2-(3,4-dimethoxyphenyl)ethyl](3-hydroxypropyl)carbamate (from Example 1) (1.99 g, 5.87 mmol), and PPh3 (1.54 g, 5.87 mmol) in THF (14.7 mL). The reaction mixture was stirred at 25° C. for 30 min, then was concentrated under reduced pressure. The residue was purified twice by flash chromatography (40-63μ silica gel) first with hexane:EtOAc 1:1 and then with CH2Cl2:acetone 95:5 to give the title compound (789.6 mg, 35% yield).

Workup

concentrationwas concentrated under reduced pressure
customThe residue was purified twice by flash chromatography (40-63μ silica gel) first with hexane:EtOAc 1:1

Sources & evidence

ORD record: ord-bcb4bf4aae8248a59cd7101d1979bfe8
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323567B2

Reaction notes

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