Tert-Butyl nitrite → HCID 10183404, compound

HRID 1826984Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([Br:25])[CH:16]=3)=[C:7]([C:13]#[N:14])[C:8](=[NH:12])[O:9]2)=[CH:4][CH:3]=1.C(ON=O)(C)(C)C.NC1C=C2C(C(C3C=C(OC)C(OC)=C(Br)C=3)=C(C#N)C(=N)O2)=CC=1>C(#N)C.CCOC(C)=O>[NH2:12][C:8]1[O:9][C:10]2[C:5]([CH:6]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([Br:25])[CH:16]=3)[C:7]=1[C:13]#[N:14])=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=2

Participants

Conditions

Temperature: 0 °C

Procedure

7-Bromo-4-(3-bromo-4,5-dimethoxy-phenyl)-3-cyano-2-imino-2H-chromene: To a suspension of t-butyl-nitrite (34 mg, 0.33 mmol), CuBr2 (68 mg, 0.30 mmol) in anhydrous acetonitrile (1.5 mL) at 0° C. was added 7-amino-3-cyano-2-imino-4-(3-bromo-4,5-dimethoxy-phenyl)-2H-chromene (100 mg, 0.25 mmol). The mixture was stirred at 0° C. for 4 h, then was diluted with EtOAc (50 mL), washed with saturated NaHCO3 (25 mL), brine (10 mL), dried over MgSO4, and evaporated to yield a yellow solid. The crude was purified by column chromatography (silica gel, EtOAc:hexanes, 1:2 to 1:1) to yield 50 mg (43%) of the title compound as a yellow solid. 1H NMR (CDCl3): 7.82 (brs, 1H), 7.38 (m, 1H), 7.30 (dd, J=2.1, 8.7 Hz, 1H), 7.18 (d, J=2.1 Hz, 1H), 7.09 (d, J=9.0 Hz, 1H), 6.93 (m, 1H), 3.96 (s, 3H), 3.92 (s, 3H).

Workup

washwashed with saturated NaHCO3 (25 mL), brine (10 mL)
dry with materialdried over MgSO4
customevaporated
customto yield a yellow solid
customThe crude was purified by column chromatography (silica gel, EtOAc:hexanes, 1:2 to 1:1)

Sources & evidence

ORD record: ord-e0ef31eb77df43e9a5d488c99f3a59bd
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053117B2

Reaction notes

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