N-bromobutanimide → Tert-butyl 3-(6-amino-5-bromopyridin-3-yl)pyrrolidine-1-carboxylate

HRID 595817Notes

Reaction equation

HRID 595817 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:27])C(=O)C1>C(#N)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]2)=[CH:4][C:3]=1[Br:27]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66742238Tert-butyl 3-(6-aminopyridin-3-yl)pyrrolidine-1-carboxylate

Product 1

HCID 118045605Tert-butyl 3-(6-amino-5-bromopyridin-3-yl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To tert-butyl 3-(6-aminopyridin-3-yl)pyrrolidine-1-carboxylate(60 mg, 0.228 mmol) in Acetonitrile (4 mL) in ice bath was added NBS (36.5 mg, 0.205 mmol) and stirred. LCMS after 30 min showed ˜1:1 mixture of starting material and desired product. To this added 12 mg (0.3 equiv.) of NBS and stirred 30 min. LCMS shows complete reaction. To the reaction mixture was added aqueous saturated NaHCO3 stirred 10 min and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered off, and evaporated. The crude product was used for next step without purification (65 mg, 83%). LCMS (m/z): 342.1/344.1 (MH+), 0.624 min.

Sources & evidence

ORD record
ord-2a398e8aa35e47b9a62ff264bfd6e722
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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