N-bromobutanimide → HCID 86670280, compound

HRID 472841Notes

Reaction equation

HRID 472841 reaction equation
[C:1]([O:5][CH:6]([C:11]1[C:12]([CH3:27])=[N:13][C:14]2[N:15]([N:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:20]=2)[C:16]=1[Cl:17])[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:35])C(=O)C1>C(#N)C>[Br:35][C:20]1[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:18][N:15]2[C:16]([Cl:17])=[C:11]([CH:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:7]([O:9][CH3:10])=[O:8])[C:12]([CH3:27])=[N:13][C:14]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86670264Methyl 2-(tert-butoxy)-2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

Product 1

HCID 86670280HCID 86670280, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 2-(tert-butoxy)-2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (800 mg, 2.063 mmol) in acetonitrile (20 mL) was added NBS (367 mg, 2.063 mmol). The reaction mixture was stirred at r.t. for 1 h. The solvent was evaported and the residue was purified by silica gel chromatography to afford (920 mg, 96%) of the title compound. 1H NMR (500 MHz, CHLOROFORM-d) δ 8.09 (dd, J=8.1, 1.4 Hz, 2H), 7.61-7.39 (m, 3H), 5.65 (s, 1H), 3.73 (s, 3H), 2.73 (s, 3H), 1.26 (s, 9H).

Workup

  1. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-97ded817e800444e8963b7bc6cd52808
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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