Potassium Iodide → HCID 58891826, compound

HRID 1768453Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:9]([Br:10])=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=1[N+:12]([O-:14])=[O:13].C[CH2:17][C:18](Br)([CH3:22])[C:19]([O-:21])=[O:20].[C:24](=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:9]([Br:10])=[CH:8][CH:7]=[C:6]([NH:11][C:18]([C:19]([O:21][CH3:24])=[O:20])([CH3:22])[CH3:17])[C:5]=1[N+:12]([O-:14])=[O:13]

Participants

Reactant 4

HCID 4875Potassium Iodide

HCID 10796Cesium carbonate

HCID 22250063HCID 22250063, compound

HCID 58891824Methyl 3-amino-6-bromo-2-nitrobenzoate

Product 1

HCID 58891826HCID 58891826, compoundYield 20%

Procedure

A solution of 3-amino-6-bromo-2-nitro-benzoic acid methyl ester (iv) (4.55 g, 16.54 mmol), methyl-bromoisobutyrate (21.0 mL, 162.29 mmol), cesium carbonate(21.94 g, 67.34 mmol), and potassium iodide (2.90 g, 17.44 mmol) was heated at 85° C. for 48 h and cooled to room temperature. The reaction mixture was partitioned between EtOAc (300 mL) and H2O (300 mL). The organic layer was washed with H2O (3×100 mL), brine and dried with Na2SO4. The solvents were removed under vacuum and the residue purified by flash column chromatography (silica gel, EtOAc/hexane) to yield the desired product v as an orange solid (1.23 g, 20%). 1H NMR (CDCl3): δ 8.22 (br s, 1H), 7.42 (d, J=9.0 Hz, 1H), 6.45 (d, J=9.0 Hz, 1H), 3.90 (s, 3H), 3.65 (s, 3H), 1.49 (s, 6H). Anal. Calcd for C13H15BrN2O6: C, 41.62; H, 4.03; N, 7.47. Found: C, 41.58; H, 3.93; N, 7.38.

Workup

customThe reaction mixture was partitioned between EtOAc (300 mL) and H2O (300 mL)
washThe organic layer was washed with H2O (3×100 mL), brine
dry with materialdried with Na2SO4
customThe solvents were removed under vacuum
customthe residue purified by flash column chromatography (silica gel, EtOAc/hexane)

Sources & evidence

ORD record: ord-c5c9cf8542494d7589d61296dc8a0aa9
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235662B2

Reaction notes

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