Cesium carbonate → tert-butyl 7-(4-iodo-1H-pyrazol-1-yl)-2-azaspiro[3.5]nonane-2-carboxylate

HRID 587128Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-iodo-1H-pyrazole and tert-butyl 7-(methylsulfonyloxy)-2-azaspiro[3.5]nonane-2-carboxylate (70 mg, 0.219 mmol, 1.0 equiv) and 4-iodo-1H-pyrazole in DMF (1 mL) was added Cs2CO3 (79 mg, 0.241 mmol, 1.1 equiv). The mixture was stirred at 80° C. for 3 hrs. It was concentrated by rotary evaporator in vacuo to give the residue which was purified by CombiFlash (12 g silica gel column, EtOAc/Hex: 0-40%) to afford 74 mg (yield 81%) of tert-butyl 7-(4-iodo-1H-pyrazol-1-yl)-2-azaspiro[3.5]nonane-2-carboxylate as a off-white solid.

Workup

concentrationIt was concentrated by rotary evaporator in vacuo
customto give the residue which
customwas purified by CombiFlash (12 g silica gel column, EtOAc/Hex: 0-40%)

Sources & evidence

ORD record: ord-a6f08ef939234673877de5e41400c1d1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226923B2

Reaction notes

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