Phosphorus oxybromide → HCID 86687897, compound

HRID 868982Notes

Reaction equation

HRID 868982 reaction equation
[CH3:1][C:2]1[N:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=O)[NH:7]2.P(Br)(Br)([Br:16])=O.C(=O)(O)[O-].[Na+]>>[Br:16][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[C:9]([CH3:12])[CH:10]=[N:11][C:2]=2[CH3:1])[N:7]=1

Participants

4

Reactant 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 701163661,6-Naphthyridin-2(1H)-one, 5,8-dimethyl-

Product 1

HCID 86687897HCID 86687897, compoundYield 22.1%

Conditions

Temperature
110 °C

Procedure

A mixture of 5,8-dimethyl-1,6-naphthyridin-2(1H)-one (2.1 g, 12 mmol) and phosphoryl tribromide (5 g) was heated to 110° C. for 1 h, cooled, diluted with ice water, and neutralized with saturated sodium bicarbonate solution. The aqueous phase was extracted with DCM (100 mL×3), and the combined organic layers were dried with sodium sulfate and purified by column chromatography to give 0.63 g of the product as a pale white solid. MS (ESI): m/z 237.0 [M+H]+.

Workup

  1. temperaturecooled
  2. extractionThe aqueous phase was extracted with DCM (100 mL×3)
  3. dry with materialthe combined organic layers were dried with sodium sulfate
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-f5fb156861a14d9cb5cf1a84f223b40e
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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