Cesium carbonate → HCID 71240179, compound

HRID 587131Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.CS(O[CH:12]1[CH2:15][C:14]2([CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]2)[CH2:13]1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH:12]2[CH2:13][C:14]3([CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]3)[CH2:15]2)[CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-bromo-1H-pyrazole (210 mg, 1.428 mmol, 1.2 equiv) and tert-butyl 2-(methylsulfonyloxy)-6-azaspiro[3.5]nonane-6-carboxylate (380 mg, 1.19 mmol, 1.0 equiv) in DMF (2.5 mL) was added Cs2CO3 (465 mg, 1.428 mmol, 1.2 equiv). The mixture was stirred at 80° C. for 3 hrs. It was concentrated by rotary evaporator to give the residue which was purified by CombiFlash (25 g silica gel column, EtOAc/Hex: 0-40%) to afford 110 mg (yield 25%) of tert-butyl 2-(4-bromo-1H-pyrazol-1-yl)-6-azaspiro[3.5]nonane-6-carboxylate (cis and trans isomers) as a colorless oil.

Workup

concentrationIt was concentrated by rotary evaporator
customto give the residue which
customwas purified by CombiFlash (25 g silica gel column, EtOAc/Hex: 0-40%)

Sources & evidence

ORD record: ord-493b1288690a4500bc2f8736d18d8ecb
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226923B2

Reaction notes

Loading…