Tryptamine → Methyl 3-(4-{[2-(1H-indol-3-yl)-ethylamino]-methyl}-phenyl)-acrylate

HRID 852896Notes

Reaction equation

HRID 852896 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)=O.[NH2:15][CH2:16][CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>ClCCCl>[NH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([CH2:17][CH2:16][NH:15][CH2:1][C:3]2[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=2)=[CH:19]1

Participants

6

Reactant 4

HCID 1150TryptamineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 53401287Methyl 3-(4-formylphenyl)-2-propenoate

Product 1

HCID 59036879Methyl 3-(4-{[2-(1H-indol-3-yl)-ethylamino]-methyl}-phenyl)-acrylateYield 83.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of 1 (3.00 g, 15.77 mmol) and tryptamine (2.78 g, 17.35 mmol) in anhydrous 1,2-dichloroethane (200 mL) under nitrogen was added NaBH(OAc)3 (3.87 g, 17.35 mmol) at room temperature. The reaction mixture was stirred at room temperature for 39 hours, poured into 10% solution of K2CO3 and extracted with CH2Cl2. The organic layer was concentrated to form a residue which was purified by flash chromatography on silica gel (MeOH/CH2Cl2, 10/90) and co-precipitated in a mixture of AcOEt/hexane to afford the title compound 2 (4.39 g, 13.13 mmol, 83% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.78 (s, 1H), 7.70-7.62 (m, 3H), 7.49 (d, J=8.0 Hz, 1H), 7.39 (d, J=8.2 Hz, 2H), 7.33 (dt, J=8.0, 0.9 Hz, 1H), 7.13 (d, J=2.2 Hz, 1H), 7.06 (ddd, J=7.0, 7.0, 1.2 Hz, 1H), 6.96 (ddd, J=6.9, 6.9, 1.1 Hz, 1H), 6.62 (d, J=16.0 Hz, 1H), 3.79 (s, 2H), 3.75 (s, 3H), 2.91-2.78 (m, 4H), 2.18 (bs, 1H).

Workup

  1. extractionextracted with CH2Cl2
  2. concentrationThe organic layer was concentrated
  3. customto form a residue which
  4. customwas purified by flash chromatography on silica gel (MeOH/CH2Cl2, 10/90)
  5. additionco-precipitated in a mixture of AcOEt/hexane

Sources & evidence

ORD record
ord-54169c5bf26e4e16907e3812d6c8ed64
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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