Formaldehyde → 2-(4,5-Dihydro-1,3-thiazol-2-yl)-N-methyl-1H-indole-7-amine

HRID 1851397Notes

Reaction equation

HRID 1851397 reaction equation
[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:15].C=O.N1C2C=CC=C[C:21]=2N=N1.O>C(O)C.O1CCCC1>[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH:15][CH3:21]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 579017772-(4,5-Dihydro-1,3-thiazol-2-yl)-1H-indole-7-amineHCID 178418385HCID 178418385, compound

Product 1

HCID 579015872-(4,5-Dihydro-1,3-thiazol-2-yl)-N-methyl-1H-indole-7-amineYield 31.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(4,5-Dihydro-1,3-thiazol-2-yl)-1H-indole-7-amine (1.08 g), aqueous formaldehyde solution (37%, 372 μL) and benzotriazole (595 mg) were dissolved in ethanol (15 mL) and tetrahydrofuran (15 mL), and the mixture was stirred at room temperature for 2 days. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give a yellow oil (360 mg, yield 31%). M+1=232.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f409d5ed5b564901aa42b152017630bb
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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