N-bromobutanimide → 7-Bromo-5-methyl-[1,3]oxazolo[4,5-c]pyridin-4-one

HRID 575712Notes

Reaction equation

HRID 575712 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]2[O:8][CH:9]=[N:10][C:4]=2[C:3]1=[O:11].C1C(=O)N([Br:19])C(=O)C1>CC#N>[Br:19][C:6]1[C:5]2[O:8][CH:9]=[N:10][C:4]=2[C:3](=[O:11])[N:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1180217925-Methyl-[1,3]oxazolo[4,5-c]pyridin-4-one

Product 1

HCID 847260897-Bromo-5-methyl-[1,3]oxazolo[4,5-c]pyridin-4-oneYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the title compound of step 4 (100 mg, 0.7 mmol) in CH3CN (5 mL) was added NBS (154 mg, 0.8 mmol) at 20° C. After 2 h, the mixture was concentrated in vacuum at 45° C. Purification by silica gel chromatography (PE:EA=5:12:1) to gave the title compound (70 mg, yield: 45%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.04 (s, 1H), 7.52 (s, 1H), 3.69 (s, 3H).

Workup

  1. concentrationthe mixture was concentrated in vacuum at 45° C
  2. customPurification by silica gel chromatography (PE:EA=5:12:1)

Sources & evidence

ORD record
ord-2697d48c9cba4d8c98d3a64013ea47de
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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