Trifluoroacetic acid → 2-(4-chloro-2-methoxy-pyridin-3-yl)-1H-indol-6-ylamine

HRID 1051216Notes

Reaction equation

HRID 1051216 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:17]3[C:18]([O:24][CH3:25])=[N:19][CH:20]=[CH:21][C:22]=3[Cl:23])[NH:14]2)=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:23][C:22]1[CH:21]=[CH:20][N:19]=[C:18]([O:24][CH3:25])[C:17]=1[C:13]1[NH:14][C:15]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([NH2:7])[CH:16]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90102920[2-(4-chloro-2-methoxy-pyridin-3-yl)-1H-indol-6-yl]-carbamic acid tert-butyl ester

Product 1

HCID 901028912-(4-chloro-2-methoxy-pyridin-3-yl)-1H-indol-6-ylamineYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [2-(4-chloro-2-methoxy-pyridin-3-yl)-1H-indol-6-yl]-carbamic acid tert-butyl ester (160 mg, 0.43) in CH2Cl2 (5 mL) was added 2,2,2-trifluoroacetic acid (0.5 mL) at 25° C. The solution was heated to reflux for 3 hours. Concentrate the solution in vacuo to afford crude 2-(4-chloro-2-methoxy-pyridin-3-yl)-1H-indol-6-ylamine (105 mg, 90%) as light yellow oil. The crude product was used directly for next step. MH+ 273.9.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 3 hours
  3. concentrationConcentrate the solution in vacuo

Sources & evidence

ORD record
ord-9cfc0a3644124d9b8558e7eafcae5212
Source dataset
uspto-grants-2016_07
Patent number
US09388166B2

Reaction notes

Loading…