1-Methylindole → HCID 57936241, compound

HRID 1435022Notes

Reaction equation

HRID 1435022 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.C([Li])CCC.Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]2[CH2:29][C:28]([CH3:31])([CH3:30])[NH:27][C:26]([CH3:33])([CH3:32])[CH2:25]2)[N:18]=1>C1COCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:21]1[CH:22]=[CH:17][N:18]=[C:19]([NH:23][CH:24]2[CH2:29][C:28]([CH3:31])([CH3:30])[NH:27][C:26]([CH3:33])([CH3:32])[CH2:25]2)[N:20]=1

Participants

5

Reactant 3

HCID 117811-Methylindole2×HCID 57936167(4-Chloro-pyrimidin-2-yl)(2,2,6,6-tetramethyl-piperidin-4-yl)-amineHCID 178418339Butyllithium2×

Product 1

HCID 57936241HCID 57936241, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-methyl-indole (244 mg, 1.86 mmol) in 10 ml of THF was treated with n-butyllithium (0.74 ml of a 2.5M solution in hexanes, 1.86 mmol) at −78° C. and the mixture was stirred under argon for 2 hours. In the meantime, a solution of (4-chloro-pyrimidin-2-yl)-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine (250 mg, 0.93 mmol) in 10 ml of THF was treated with n-butyllithium (0.74 ml of 2.5M solution in hexanes, 1.86 mmol) at −78° C. under argon for 15 minutes and the above solution containing the lithiated 1-methyl-indole was added with a syringe. The reaction mixture was stirred for 15 minutes at 0° C. and for 2 hours at room temperature. The reaction was quenched with saturated ammonium chloride solution (5 ml) and extracted with EtOAc. The organic layer was dried over sodium sulfate and evaporated. Purification by column chromatography on silicagel (EtOAc/MeOH/ammonia:2/1/0.02) gave the title compound. Yield: 92.5 mg (27%).

Workup

  1. additionwas added with a syringe
  2. stirringThe reaction mixture was stirred for 15 minutes at 0° C. and for 2 hours at room temperature
  3. customThe reaction was quenched with saturated ammonium chloride solution (5 ml)
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customevaporated
  7. customPurification by column chromatography on silicagel (EtOAc/MeOH/ammonia:2/1/0.02)

Sources & evidence

ORD record
ord-5911a2fd151848b69a1f13de98ea229c
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

Loading…