1,1-Dichloroethane → HCID 18382802, compound

HRID 2297831Notes

Reaction equation

HRID 2297831 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][CH:13]=[CH:14][N:15]=3)[S:10][C:3]=12.[CH3:16][C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([NH2:26])=[CH:21][CH:20]=2.ClC(Cl)C>C(O)(C)(C)C>[CH3:16][C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([NH:26][C:2]1[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[S:12][CH:13]=[CH:14][N:15]=4)[S:10][C:3]=13)=[CH:21][CH:20]=2

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 27339925-Amino-2-methylindoleHCID 221436637-Chloro-2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridine

Product 1

HCID 18382802HCID 18382802, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

7-Chloro-2-thiazol-2-yl-thieno[3,2-b]pyridine (400 mg, 1.58 mmol) and 2-methyl-5-aminoindole (231 mg, 1.58 mmol) were dissolved in 6 mL of t-butyl alcohol and 6 mL of dichloroethane and the solution was heated to 85° C. After allowing the reaction to go dry overnight the reaction mixture was cooled and absorbed onto silica gel. Chromatography of the residue with 5% methanol:methylene chloride afforded 374 mg (68%) (2-methyl-1H-indol-5-yl)-(2-thiazol-2-yl-thieno[3,2-b]pyridin-7-yl)-amine. 1H NMR (400 MHz, DMSO) δ8.78 (s, 1H), 8.18 (d, 1H), 7.84 (m, 2H), 7.27 (m, 2H), 6.90 (d, 1H), 7.39 (d, 1H), 6.59 (d, 1H), 6.10 (s, 1H), 2.36 (s, 3H). LC-MS: 363 (MH+); HPLC RT: 5.01 min.

Workup

  1. customthe reaction
  2. customto go dry overnight the reaction mixture
  3. temperaturewas cooled
  4. customabsorbed onto silica gel

Sources & evidence

ORD record
ord-7c6514c1ce4648b88afc35d889a6ad48
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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