1,1-Dichloroethane → 2-(1-Methyl-1H-imidazol-5-yl)-N-(2-methyl-1H-indol-5-yl)thieno(3,2-b)pyridin-7-amine

HRID 2297827Notes

Reaction equation

HRID 2297827 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]([CH3:16])[CH:13]=[N:14][CH:15]=3)[S:10][C:3]=12.[CH3:17][C:18]1[NH:19][C:20]2[C:25]([CH:26]=1)=[CH:24][C:23]([NH2:27])=[CH:22][CH:21]=2.ClC(Cl)C>C(O)(C)(C)C>[CH3:16][N:12]1[C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[NH:27][C:23]3[CH:24]=[C:25]4[C:20](=[CH:21][CH:22]=3)[NH:19][C:18]([CH3:17])=[CH:26]4)[CH:8]=2)=[CH:15][N:14]=[CH:13]1

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 27339925-Amino-2-methylindoleHCID 222500727-chloro-2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridine

Product 1

HCID 183828032-(1-Methyl-1H-imidazol-5-yl)-N-(2-methyl-1H-indol-5-yl)thieno(3,2-b)pyridin-7-amineYield 16.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

7-Chloro-2-(3-methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridine (600 mg, 2.40 mmol) and 2-methyl-5-aminoindole (422 mg, 2.89 mmol) were dissolved in 20 mL of tert-butanol and 20 mL of dichloroethane and heated to 85° C. The solvent was allowed to evaporate overnight and was replaced the following day with the same amounts as in the initial reaction mixture along with an additional 90 mg of the indole. The solution was heated an additional 24 hours and allowed to go dry as before. Chromatography of the residue with 30-5-% methanol:ethyl acetate afforded 142 mg (16%) of [2-(3-methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridin-7-yl]-(2-methyl-1H-indol-5-yl)-amine. 1H NMR (400 MHz, CD3OD) δ8.14 (d, 1H), 7.79 (s, 1H), 7.75 (s, 1H), 7.40 (s, 1H), 7.34 (d, 1H), 7.29 (s, 1H), 6.99 (d, 1H), 6.72 (d, 1H), 6.17 (s, 1H), 3.84 (s, 3H), 2.44 (s, 3H). LC-MS: 360, 361 (MH+); HPLC RT: 3.96 min.

Workup

  1. customto evaporate overnight
  2. customreaction mixture along with an additional 90 mg of the indole
  3. temperatureThe solution was heated an additional 24 hours
  4. customto go dry as before

Sources & evidence

ORD record
ord-02bcda9fa3524a8c9ebdaa59678633a9
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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