Triethylamine → 4-[(4-Methyl-1H-indol-5-yl)amino]-5-(1,3-thiazol-2-yl)nicotinonitrile

HRID 506199Notes

Reaction equation

HRID 506199 reaction equation
I[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:9]=1[NH:10][C:11]1[C:12]([CH3:20])=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[C:7]#[N:8].C([Sn](CCCC)(CCCC)[C:26]1[S:27][CH:28]=[CH:29][N:30]=1)CCC.C(N(CC)CC)C>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:20][C:12]1[C:11]([NH:10][C:9]2[C:6]([C:7]#[N:8])=[CH:5][N:4]=[CH:3][C:2]=2[C:26]2[S:27][CH:28]=[CH:29][N:30]=2)=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][NH:16]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 684438315-iodo-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile

Product 1

HCID 684648364-[(4-Methyl-1H-indol-5-yl)amino]-5-(1,3-thiazol-2-yl)nicotinonitrile

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-iodo-4[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile (120 mg, 0.32 mmol), 2-(tributylstannyl)-1,3-thiazole (340 mg, 0.91 mmol), dichlorobis(triphenylphosphine)palladium(II) (28 mg, 0.04 mmol), and triethylamine (36 mg, 0.35 mmol) in dioxane (4 mL) was heated at reflux for 24 h. 4-[(4-Methyl-1H-indol-5-yl)amino]-5-(1,3-thiazol-2-yl)nicotinonitrile was obtained following the work-up and purification procedures as described for the preparation of 5-(2-formyl-1-methyl-1H-imidazol-5-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile 541. HPLC retention time: 10.1 min.(g); MS: 332.2 (M+H); melting range: 245-247° C.; and HRMS: 332.0964.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h

Sources & evidence

ORD record
ord-f48aea25ab0e4ef68afb2a1ee0a466b8
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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