Triphenylphosphine → 8-[2-(4-Bromo-2-methylphenoxy)ethyl]-11-ethyl-5,11-dihydro-5-methyl-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 393286Notes

Reaction equation

CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH2:15]([N:17]1[C:23]2[N:24]=[CH:25][C:26]([CH2:28][CH2:29][OH:30])=[CH:27][C:22]=2[C:21](=[O:31])[N:20]([CH3:32])[C:19]2[CH:33]=[CH:34][CH:35]=[N:36][C:18]1=2)[CH3:16].[Br:37][C:38]1[CH:43]=[CH:42][C:41](O)=[C:40]([CH3:45])[CH:39]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[Br:37][C:38]1[CH:43]=[CH:42][C:41]([O:30][CH2:29][CH2:28][C:26]2[CH:25]=[N:24][C:23]3[N:17]([CH2:15][CH3:16])[C:18]4[N:36]=[CH:35][CH:34]=[CH:33][C:19]=4[N:20]([CH3:32])[C:21](=[O:31])[C:22]=3[CH:27]=2)=[C:40]([CH3:45])[CH:39]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of DIAD (0.44 mL, 2.40 mmol) in THF (1.0 mL) was added dropwise to an ice-cold solution of 11-ethyl-5,11-dihydro-8-(2-hydroxyethyl)-5-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (480 mg, 1.61 mmol), 4-bromo-2-methylphenol (318 mg, 1.70 mmol) and PPh3 (629 mg, 2.40 mmol) in THF (20 mL) at 25° C. The mixture was stirred at 0° C. for 3 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (Hexane:EtOAc, 7:3) to yield the title compound (437 mg, 58% yield) as a white solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by flash chromatography (Hexane:EtOAc, 7:3)

Sources & evidence

ORD record: ord-a979fae8f585431db5b0da04f5a05ea0
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06806265B2

Reaction notes

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