1-Bromo-3-chloropropane → 9-(3-Chloro-1-propyl)-3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-9H-beta-carboline

HRID 355818Notes

Reaction equation

HRID 355818 reaction equation
[CH:1]1([C:4]2[N:8]=[C:7]([C:9]3[N:10]=[CH:11][C:12]4[NH:13][C:14]5[C:19]([C:20]=4[CH:21]=3)=[CH:18][CH:17]=[CH:16][CH:15]=5)[O:6][N:5]=2)[CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:25][CH2:26][CH2:27][Cl:28]>CN(C=O)C>[Cl:28][CH2:27][CH2:26][CH2:25][N:13]1[C:12]2[CH:11]=[N:10][C:9]([C:7]3[O:6][N:5]=[C:4]([CH:1]4[CH2:3][CH2:2]4)[N:8]=3)=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 189407253-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-9H-beta-carboline

Product 1

HCID 189407279-(3-Chloro-1-propyl)-3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-9H-beta-carbolineYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound was synthesized by mixing (Compound 5) (1.0 g, 3.6 mmol), NaH (0.22 g, 4.3 mmol) and 1-bromo-3-chloropropane (0.68 g, 4.3 mmol)in DMF, in the same manner as illustrated in example 3, to give the title compound (0.76 g, 63%) as a white solid. M.p. 165°-169° C.

Workup

  1. customThe compound was synthesized

Sources & evidence

ORD record
ord-3b42a3b6c08943bd8f053981f54051b6
Source dataset
uspto-grants-1998_11
Patent number
US05834482

Reaction notes

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