Triethylamine → HCID 89421807, compound

HRID 1481738Notes

Reaction equation

HRID 1481738 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]([CH3:25])[C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([C:20](=O)[CH2:21][CH2:22][CH3:23])=[CH:15][CH:14]=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:26][O:27][C:28]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:29]=1[CH2:30][NH2:31].CCN(CC)CC>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]([CH3:25])[C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([C:20](=[N:31][CH2:30][C:29]1[CH:32]=[CH:33][C:34]([O:36][CH3:37])=[CH:35][C:28]=1[O:27][CH3:26])[CH2:21][CH2:22][CH3:23])=[CH:15][CH:14]=2)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5972502,4-DimethoxybenzylamineHCID 71285237HCID 71285237, compound

Product 1

HCID 89421807HCID 89421807, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To solution of 1-(2-(2-(tert-butyldimethylsilyloxy)ethyl)-1-methyl-1H-indol-5-yl)butan-1-one (6.62 g, 18.41 mmol) in DCM (35 mL) was added 2,4-dimethoxybenzylamine (3.20 mL, 21.30 mmol) and NEt3 (7.0 mL, 50.22 mmol). Mixture was cooled to 0° C. before TiCl4 solution (1M DCM, 12.0 mL, 12.0 mmol) was added dropwise via syringe pump over 30 min. Reaction was allowed to warm to room temperature and stirred overnight. Mixture was diluted with DCM (100 mL) and then quenched with NaHCO3 (aqueous saturated, ˜30 mL). Upon vigorous shaking organic phase was separated using PTFE phase separator and dried over Na2SO4. Removal of the solvent afforded N-(1-(2-(2-(tert-butyldimethylsilyloxy)ethyl)-1-methyl-1H-indol-5-yl)butylidene)-1-(2,4-dimethoxyphenyl)methanamine as yellow oil, which was taken directly into next step without purification.

Workup

  1. additionwas added dropwise via syringe pump over 30 min
  2. customReaction
  3. customquenched with NaHCO3 (aqueous saturated, ˜30 mL)
  4. customUpon vigorous shaking organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-2258c00a7a284a77b0e1331a2ec6cf65
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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