Cesium carbonate → HCID 90386938, compound

HRID 1476919Notes

Reaction equation

[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:21]1[N:26]=[C:25]([C:27]#[N:28])[CH:24]=[CH:23][C:22]=1[CH3:29]>CN1C(=O)CCC1>[C:27]([C:25]1[N:26]=[C:21]([O:1][C@H:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]2)[C:22]([CH3:29])=[CH:23][CH:24]=1)#[N:28]

Participants

Conditions

Temperature: 140 °C

Procedure

To (S)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (491 mg, 2.62 mmol) in NMP (4 mL) was added Cs2CO3 (1025 mg, 3.15 mmol). The mixture was stirred at 0° C. for 1 hour at which time 6-chloro-5-methylpicolinonitrile (400 mg, 2.62 mmol) was added. The reaction mixture was heated at 140° C. for 1 hour in a microwave reactor to give the title compound in a crude reaction mixture that was used directly in the next step.

Workup

additionwas added

Sources & evidence

ORD record: ord-f233ff50f30d4a2383890ec748a4098d
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09402841B2

Reaction notes

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