Nitrogen → 2-Methyl-5-{2-nitro-4-[2-(3,4,5-trihydroxy-phenyl)-acetylamino]-phenyl}-furan-3-carboxylic acid

HRID 383596Notes

Reaction equation

N#N.[CH3:3][C:4]1[O:5][C:6]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:33])[CH2:20][C:21]3[CH:26]=[C:25]([O:27]C)[C:24]([O:29]C)=[C:23]([O:31]C)[CH:22]=3)=[CH:14][C:13]=2[N+:34]([O-:36])=[O:35])=[CH:7][C:8]=1[C:9]([OH:11])=[O:10].B(Br)(Br)Br.O>C(Cl)Cl.CO>[CH3:3][C:4]1[O:5][C:6]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:33])[CH2:20][C:21]3[CH:26]=[C:25]([OH:27])[C:24]([OH:29])=[C:23]([OH:31])[CH:22]=3)=[CH:14][C:13]=2[N+:34]([O-:36])=[O:35])=[CH:7][C:8]=1[C:9]([OH:11])=[O:10]

Participants

Conditions

Temperature: -78 °C

Procedure

(The following reaction is done in an anhydrous N2 atmosphere.) Dissolve 2-Methyl-5-{2-nitro-4-[2-(3,4,5-trimethoxy-phenyl)-acetylamino]-phenyl}-furan-3-carboxylic acid (60) (33 mg, 0.07 mmol) in anhydrous DCM (1.0 mL), cool the solution to −78° C. and add dropwise BBr3 (66 μL, 0.70 mmol). Stir the reaction mixture for 10 min at −78° C. and after slowly warming up for additional 2 h at rt. Cool reaction mixture to 0° C., add dropwise water and DCM followed by MeOH to homogenize the mixture and remove solvent. Suspend the crude product in MeOH and filtrate it through a short pad of celite to obtain 2-Methyl-5-{2-nitro-4-[2-(3,4,5-trihydroxy-phenyl)-acetylamino]-phenyl}-furan-3-carboxylic acid (61) (22 mg, 72%) as a brown solid. 1H NMR (400 MHz, CD3OD): 2.62 (s, 3H); 3.53 (s, 2H); 6.40 (s, 2H); 6.88 (s, 1H); 7.73 (d, 1H, J=8.6 Hz); 7.80 (dd, 1H, J1=8.6 Hz, J2=2.0 Hz); 8.24 (d, 1H, J=2.0 Hz).

Workup

custom(The following reaction
temperatureafter slowly warming up for additional 2 h at rt
temperatureCool
customreaction mixture to 0° C.
stirringto homogenize the mixture
customremove solvent

Sources & evidence

ORD record: ord-773ec6ac2c5645b6a6827a4efff4d4ce
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367677B2

Reaction notes

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