Cesium carbonate → HCID 90386995, compound

HRID 1476916Notes

Reaction equation

HRID 1476916 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][CH:22]=1>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)[CH:22]=[CH:23][CH:24]=1)#[N:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1184246-Chloropyridine-2-carbonitrileHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 90386995HCID 90386995, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

To (S)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (676 mg, 3.61 mmol) in NMP (4 mL) at 0° C. was added Cs2CO3 (1176 mg, 3.61 mmol) followed by 6-chloropicolinonitrile (500 mg, 3.61 mmol). The mixture was heated at 140° C. for 15 minutes in a microwave reactor to give the title compound. The crude product was used directly in the next step.

Sources & evidence

ORD record
ord-3ddaca36de534814a91f8a9ebbb87018
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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