Cesium carbonate → HCID 58547111, compound

HRID 1850240Notes

Reaction equation

HRID 1850240 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[C:11]([Br:12])=[CH:10][CH:9]=[CH:8][N:7]=2)[CH2:3]1.Cl[C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Br:12][C:11]1[C:6]([CH:4]2[CH2:3][N:2]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=3)[CH2:5]2)=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 119282-ChloroquinolineHCID 67469068HCID 67469068, compound

Product 1

HCID 58547111HCID 58547111, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-(azetidin-3-yl)-3-bromopyridine hydrochloride (4) (221 g, 0.886 mol), 2-chloroquinoline (133.5 g, 0.816 mol, 0.92 eq., Combi-Blocks) and cesium carbonate (866 g, 2.658 mol, 3 eq.) in anhydrous DMF (7 L) was heated to 110° C. and stirred for 16 hrs. After cooling to RT, the mixture was transferred to 50 L separatory funnel and diluted with water (14 L). The precipitated solid was filtered, stirred in water (4 L), filtered and dried to obtain 222 g of 2-(3-(3-bromopyridin-2-yl)azetidin-1-yl)quinoline. Yield: 80% over two steps.

Workup

  1. temperatureAfter cooling to RT
  2. customthe mixture was transferred to 50 L separatory funnel
  3. filtrationThe precipitated solid was filtered
  4. stirringstirred in water (4 L)
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-38291908bea94617a1b6795570271f04
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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