Potassium Carbonate → HCID 67016364, compound

HRID 1503478Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C=O)C>[Si:19]([O:18][CH2:17][CH2:16][N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 4-nitropyrazole (904 mg, 8 mmol) and potassium carbonate (3.3 g, 24 mmol) in DMF (10 mL) was added (2-bromoethoxy)(tert-butyl)dimethylsilane (0.6 mL, 2.9 mmol) and the mixture was heated to 50° C. for 2 h. Further (2-bromoethoxy)(tert-butyl)dimethylsilane (1.4 mL, 6.7 mmol) was added and the mixture was heated to 50° C. for 4 h. The solvent was removed in vacuo and the residue was partitioned between DCM (10 mL) and water (10 mL). The organic phase was passed through a hydrophobic frit and the solvent was removed in vacuo. The residue was purified by silica gel column chromatography, eluting with iso-hexane/ethyl acetate (100/0 to 0/100), to give the title compound (2.15 g, 99%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.20 (s, 1H), 8.08 (s, 1H), 4.24 (t, J=4.9 Hz, 2H), 3.95 (t, J=4.9 Hz, 2H), 0.84 (s, 9H), −0.04 (s, 6H). LC-MS (ESCI): m/z=272 (M+H)+.

Workup

temperaturethe mixture was heated to 50° C. for 4 h
customThe solvent was removed in vacuo
customthe residue was partitioned between DCM (10 mL) and water (10 mL)
customthe solvent was removed in vacuo
customThe residue was purified by silica gel column chromatography
washeluting with iso-hexane/ethyl acetate (100/0 to 0/100)

Sources & evidence

ORD record: ord-3adf8329f78748edaef4652d59cf338c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212186B2

Reaction notes

Loading…