N-bromobutanimide → HCID 117667295, compound

HRID 712775Notes

Reaction equation

HRID 712775 reaction equation
[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:11]#[N:12].[Br:13]N1C(=O)CCC1=O>C(Cl)Cl>[Br:13][C:3]1[C:2]([C:11]#[N:12])=[N:1][C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 917551461260779-07-4

Product 1

HCID 117667295HCID 117667295, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a vial is added 5,6,7,8-tetrahydro-1,8-naphthyridine-2-carbonitrile (370 mg, 2.32 mmol) and N-bromosuccinimide (413 mg, 2.32 mmol) in 20 mL of CH2Cl2. The reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is concentrated. The residue is purified by flash column chromatography to give 550 mg of 3-bromo-5,6,7,8-tetrahydro-[1,8]naphthyridine-2-carbonitrile.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-da7317ba4f3b47d6aa73f52d53048942
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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