Methylamine → 2-Methylamino-N-phenyl-N-(1-triisopropylsilanyl-1H-indol-4-yl)-acetamide

HRID 268763Notes

Reaction equation

HRID 268763 reaction equation
Cl[CH2:2][C:3]([N:5]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][N:10]2[Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[O:4].[CH3:31][NH2:32]>>[CH3:31][NH:32][CH2:2][C:3]([N:5]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][N:10]2[Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[O:4]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 598318082-Chloro-N-phenyl-N-(1-triisopropylsilanyl-1H-indol-4-yl)-acetamide

Product 1

HCID 598318392-Methylamino-N-phenyl-N-(1-triisopropylsilanyl-1H-indol-4-yl)-acetamide

Procedure

A solution of 2-chloro-N-phenyl-N-(1-triisopropylsilanyl-1H-indol-4-yl)-acetamide XXII (192 mg, 0.435 mmol) and MeNH2 (33% w in EtOH, 2 ml) was stirred for 2.5 h. The solvent was evaporated and the residue was partitioned between EtOAc and a saturated solution of NaHCO3. The aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, concentrated, and the resulting crude 2-methylamino-N-phenyl-N-(1-triisopropylsilanyl-1H-indol-4-yl)-acetamide XXIII (180 mg) was used without further purification for the next reaction.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between EtOAc
  3. extractionThe aqueous layer was extracted twice with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe resulting crude 2-methylamino-N-phenyl-N-(1-triisopropylsilanyl-1H-indol-4-yl)-acetamide XXIII (180 mg) was used without further purification for the next reaction

Sources & evidence

ORD record
ord-c975c8f697c842d0bb97584d59581463
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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