5-Amino-2-methylindole → HCID 10156382, compound

HRID 1063133Notes

Reaction equation

HRID 1063133 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[O:12])[S:10][C:3]=12.[CH3:18][C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([NH2:28])=[CH:23][CH:22]=2>CCO>[CH3:18][C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([NH:28][C:2]1[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]([N:13]4[CH2:17][CH2:16][CH2:15][CH2:14]4)=[O:12])[S:10][C:3]=13)=[CH:23][CH:22]=2

Participants

4

Reactant 2

HCID 27339925-Amino-2-methylindoleHCID 11173165(7-Chlorothieno[3,2-b]pyridin-2-yl)(pyrrolidin-1-yl)methanone

Product 1

HCID 10156382HCID 10156382, compoundYield 112.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (7-chloro-thieno[3,2-b]pyridin-2-yl)-pyrrolidin-1-yl-methanone (0.359 g, 1.34 mmol) and 2-methyl-1H-indol-5-ylamine (0.19 g, 1.3 mmol) in EtOH (10 mL) was heated to reflux for 48 h. The reaction mixture was cooled to room temperature and concentrated onto silica gel (5 mL). Purification by flash chromatography on silica gel eluting with CH2Cl2/NEt3 (99.5/0.5) afforded the title compound as a yellow solid (550 mg) MS: 377.2 (MH+); HPLC Rf: 4.45 min; HPLC purity: 97%.

Workup

  1. temperatureto reflux for 48 h
  2. concentrationconcentrated onto silica gel (5 mL)
  3. customPurification by flash chromatography on silica gel eluting with CH2Cl2/NEt3 (99.5/0.5)

Sources & evidence

ORD record
ord-934bf86e542a4e22a4966f4b72fd29ab
Source dataset
uspto-grants-2005_11
Patent number
US06964961B2

Reaction notes

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