Cesium carbonate → HCID 86728162, compound

HRID 627729Notes

Reaction equation

HRID 627729 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([OH:12])=[CH:7]2.Br[C:14]#[C:15][CH2:16][CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:14]([O:12][C:8]1[CH:9]=[N:10][C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[N:3][C:2]=2[Cl:1])[C:15]#[C:16][CH3:17]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 109970821-Bromobut-1-yneHCID 136341362HCID 136341362, compound

Product 1

HCID 86728162HCID 86728162, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8-chloro-1,7-naphthyridin-3-ol (618 mg, 3.42 mmol) in DMF (11 ml) were added bromobutyne (882 mg, 6.67 mmol), cesium carbonate (3233 mg, 9.92 mmol). The reaction mixture was heated at 50° C. for 0.5 h. It was quenched with water, and light brown precipitate was formed. It was then collected by Buchner funnel to yield 3-(but-2-yn-1-yloxy)-8-chloro-1,7-naphthyridine (550 mg, 74% yield) as light brown solid. MS m/z: 233.1 [M+H].

Workup

  1. customIt was quenched with water
  2. customlight brown precipitate was formed
  3. customIt was then collected by Buchner funnel

Sources & evidence

ORD record
ord-67ca08232d714574a205f393f43ea89b
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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