Sodium Bicarbonate → N-(2-amino-5-(pyridin-3-yl)phenyl)pyrrolidine-1-carboxamide

HRID 2201707Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][C:3]=1[NH:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19](B(O)O)[CH:18]=1.C(=O)(O)[O-].[Na+]>C1COCC1.O.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)=[CH:4][C:3]=1[NH:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of N-(2-amino-5-bromophenyl)pyrrolidine-1-carboxamide (0.26 g, 0.72 mmol) in THF (10 mL) and water (5 mL) were added pyridin-3-ylboronic acid (0.13 g, 1.07 mmol, 1.5 equiv.), sodium bicarbonate (0.11 g, 1.07 mmol, 1.5 equiv.) and palladium(0) (0.08 g, 0.07 mmol, 0.1 equiv.). The reaction mass was stirred at 90° C. for sixteen hours. The reaction crude was filtered on a celite bed and diluted in ethyl acetate. The organic layers were washed with water and brine then dried over Na2SO4 and concentrated. The residue was purified by column chromatography on eluting ethyl acetate and hexane to allow N-(2-amino-5-(pyridin-3-yl)phenyl)pyrrolidine-1-carboxamide (0.14 g, 63% yield).

Workup

customThe reaction crude
filtrationwas filtered on a celite bed
additiondiluted in ethyl acetate
washThe organic layers were washed with water and brine
dry with materialthen dried over Na2SO4
concentrationconcentrated
customThe residue was purified by column chromatography
washon eluting ethyl acetate and hexane

Sources & evidence

ORD record: ord-2f7fc84e83604e9897f456091a5c05e2
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365498B2

Reaction notes

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