Trimethyl-(6-methylpyrazin-2-yl)stannane → tert-butyl N-[(3S)-1-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-2-oxo-3-piperidyl]carbamate

HRID 57933Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[N:16]=[C:15]([N:17]4[CH2:22][CH2:21][CH2:20][C@H:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:18]4=[O:31])[CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C[Sn](C)(C)[C:34]1[CH:39]=[N:38][CH:37]=[C:36]([CH3:40])[N:35]=1>CN(C)C(=O)C>[CH3:40][C:36]1[N:35]=[C:34]([C:2]2[N:7]=[CH:6][C:5]3[CH:8]=[N:9][N:10]([C:11]4[N:16]=[C:15]([N:17]5[CH2:22][CH2:21][CH2:20][C@H:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:27])[CH3:28])[C:18]5=[O:31])[CH:14]=[CH:13][CH:12]=4)[C:4]=3[CH:3]=2)[CH:39]=[N:38][CH:37]=1

Participants

Conditions

Temperature: 145 °C

Procedure

A solution of tert-butyl N-[(3S)-1-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]-2-oxo-3-piperidyl]carbamate (125 mg, 0.282 mmol) and palladium(0)tetrakis(triphenylphosphine) (32 mg, 0.028 mmol) in N,N-dimethylacetamide 5.0 mL was added trimethyl-(6-methylpyrazin-2-yl)stannane (145 mg, 0.565 mmol). The reaction mixture heated at 145° C. for 40 min in CEM microwave. The reaction mixture was filtered through celite and concentrated. The crude product was diluted with EtOAc then washed with water. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was carried to next step. MS (ESI) m/z: 501.1.

Workup

filtrationThe reaction mixture was filtered through celite
concentrationconcentrated
additionThe crude product was diluted with EtOAc
washthen washed with water
dry with materialThe organic layers was dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuum

Sources & evidence

ORD record: ord-acdb07c56cad45f7b3de64efa2089dd7
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Reaction notes

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