1,2-Dichloroethane → HCID 6539890, compound

HRID 225911Notes

Reaction equation

HRID 225911 reaction equation
C(Cl)CCl.Cl.N[C:7](=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([OH:10])=O.[CH3:18][N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[C:20]1[CH2:28][NH:29][CH3:30].C1C=CC2N(O)N=[N:37]C=2C=1.O.C(N(CC)CC)C>CN(C=O)C>[NH2:37][C:15]1[CH:16]=[CH:17][C:12](/[CH:11]=[CH:7]/[C:8]([N:29]([CH3:30])[CH2:28][C:20]2[N:19]([CH3:18])[C:27]3[C:22]([CH:21]=2)=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:10])=[CH:13][CH:14]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineHCID 86601546HCID 86601546, compound

Product 1

HCID 6539890HCID 6539890, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (218 mg, 1.14 mmole) was added to a solution of aminocinnamic acid hydrochloride (220 mg, 1.10 mmole), 1-methyl-2-(methylaminomethyl)-1H-indole (0.20 g, 1.15 mmole), HOBt.H2O (154 mg, 1.14 mmole), and triethylamine (0.20 mL, 1.43 mmole) in DMF (20 mL) at RT. The reaction was stirred overnight, then was concentrated in vacuo. The residue was diluted with 5% NaHCO3 and extracted with CH2Cl2. The combined organic extracts were washed with brine (2×30 mL) and dried over MgSO4. Flash chromatography on silica gel (3% MeOH/CH2Cl2) gave the title compound (68 mg, 19%) as a yellow foam: 1H NMR (360 MHz, DMSO-d6, 330K) δ 7.46 (d, J=7.8 Hz, 1 H), 7.42 (d. J=15.3 Hz, 1 H), 7.37 (d, J=8.3 Hz, 1 H), 7.32 (d, J=8.5 Hz, 2 H), 7.06-7.15 (m, 1 H), 6.94-7.03 (m, 1 H), 6.81 (d, J=15.3 Hz, 1 H), 6.58 (d, J=8.5 Hz, 2 H), 6.33 (s, 1 H), 5.25 (br s, 2 H), 4.85 (s, 2 H), 3.70 (s, 3 H), 3.02 (s, 3 H); MS (ES) m/e 320 (M+H)+.

Workup

  1. customat RT
  2. concentrationwas concentrated in vacuo
  3. additionThe residue was diluted with 5% NaHCO3
  4. extractionextracted with CH2Cl2
  5. washThe combined organic extracts were washed with brine (2×30 mL)
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-7a242ce66609486f9d068808d2aacb0d
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

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