Methanol → N-Methyl-2-(1,3-thiazol-2-yl)-N-(2-thienylmethyl)-1H-indole-7-amine

HRID 1851590Notes

Reaction equation

HRID 1851590 reaction equation
[CH3:1][N:2]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]=[CH:22][N:23]=1)=[CH:15]2)[C:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)=O.B.O1CCCC1.CO>O1CCCC1>[CH3:1][N:2]([CH2:3][C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]=[CH:22][N:23]=1)=[CH:15]2

Participants

5

Reactant 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 57901666N-methyl-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-2-carboxamide

Product 1

HCID 57901798N-Methyl-2-(1,3-thiazol-2-yl)-N-(2-thienylmethyl)-1H-indole-7-amineYield 38.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methyl-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-2-carboxamide (150 mg) in tetrahydrofuran (10 mL) was added borane-tetrahydrofuran complex (1.0 M tetrahydrofuran solution, 10 mL). The reaction mixture was stirred with heating under reflux for 1 hr. The reaction mixture was cooled to room temperature, and methanol (5 mL) was added. The reaction mixture was stirred with heating under reflux for 1 hr, and the reaction mixture was concentrated. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:3) to give the title compound (55 mg, yield 38%) as a yellow oil. M+1=326.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hr
  3. stirringThe reaction mixture was stirred
  4. temperaturewith heating
  5. temperatureunder reflux for 1 hr
  6. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-676d6b86999045759e393e1476d666f0
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

Loading…