Trimethylamine → 5-((2-chloropyrimidin-4-yl)oxy)-2-methyl-1H-indole

HRID 244518Notes

Reaction equation

HRID 244518 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[CH:5]2.[Cl:12][C:13]1[N:18]=[C:17](Cl)[CH:16]=[CH:15][N:14]=1.C([O-])(O)=O.[Na+].[OH-].[K+].[OH-].[Na+].C(N(C(C)C)CC)(C)C.CN(C)C>O1CCCC1.O1CCOCC1.CN(C)C=O.C(#N)C.C(N(CC)CC)C.N1C=CC=CC=1>[Cl:12][C:13]1[N:18]=[C:17]([O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([CH3:11])=[CH:5]3)[CH:16]=[CH:15][N:14]=1

Participants

14

Reactant 7

HCID 1146TrimethylamineHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 775312,4-Dichloropyrimidine2×HCID 81531DiisopropylethylamineHCID 833362-methyl-1H-indol-5-ol2×HCID 516892Sodium Bicarbonate

Product 1

HCID 598233595-((2-chloropyrimidin-4-yl)oxy)-2-methyl-1H-indole

Reagents, catalysts & solvents 6

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound 3 can be prepared by the reaction of 5-hydroxyl-2-methyl-indole (compound 1) with 2,4-dichloropyrimidine (compound 2) in the presence of a base, such as but not limited to NaHCO3, KOH, NaOH, K2CO2, KHCO3, diisopropylethylamine (DIPEA), pyridine, triethylamine (TEA) or trimethylamine; in a solvent, such as but not limited to acetonitrile, N,N-dimethylforamide (DMF), dioxane, tetrahydrofuran (THF). The reaction may be carried out at a suitable temperature, such as a temperature ranging from 0 to 60° C.

Workup

  1. customThe reaction
  2. customranging from 0 to 60° C.

Sources & evidence

ORD record
ord-4aa5c5a168eb4cdaad867aed6b1bf03a
Source dataset
uspto-grants-2014_02
Patent number
US08658658B2

Reaction notes

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