1,1'-(Diazomethylene)bis(benzene) → HCID 58928679, compound

HRID 853661Notes

Reaction equation

[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:9](=[C:10]([OH:27])[C:11]4[N:12]=[CH:13][CH:14]=[N:15][C:16]=4[C:17]=3[O:21][C:22](=[O:26])[O:23][CH2:24][CH3:25])[C:8]2=[O:28])=[CH:4][CH:3]=1.[C:31]1([C:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[N+]=[N-])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>ClCCCl>[CH2:24]([O:23][C:22](=[O:26])[O:21][C:17]1[C:16]2[N:15]=[CH:14][CH:13]=[N:12][C:11]=2[C:10]([O:27][CH:37]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[C:9]2[C:8](=[O:28])[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:30][CH:29]=3)[C:19](=[O:20])[C:18]=12)[CH3:25]

Participants

Conditions

Temperature: 70 °C

Procedure

Carbonic acid mono-[1-(1-benzyl-4-methylene-2,5-dioxo-pyrrolidin-3-ylidene)-ethyl]ester 243 (1.1 g, 2.68 mmol, 1 equiv.) was dissolved in 1,2 dichloroethane (50 mL, 0.055 M) and to this was added diphenyldiazomethane (1.05 g, 5.35 mmol, 2 equiv.) and heated at 70° C. under a nitrogen atmosphere for 24 hours. The reaction was concentrated in vacuo and purified by silica gel chromatography using 4/1 Hexanes/Ethyl acetate to obtain carbonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-6,8-dioxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinoxalin-5-yl ethyl ester 244 (70%, 1085 mg, 1.87 mmol). 1H NMR (300 MHz) CDCl3 δ 9.09 (d, J=6 Hz, 1 H), 8.97 (d, J=6 Hz, 1 H), 8.65 (bs, 1 H), 7.46 (d, J=4.8 Hz, 2 H),7.03 (d, J=4.8 Hz, 2 H), 4.85 (s, 2 H),4.04 (q, J=2.8 Hz,2 H), 1.43 (q, J=2.8 Hz, 3 H). MS: 600.2 (M+23). TLC Rf: 0.3 Hexanes/Ethyl acetate (7/3)

Workup

concentrationThe reaction was concentrated in vacuo
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-902471734736499d9f409aaf2538adb9
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253180B2

Reaction notes

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