1,2-Dichloroethane → HCID 12125396, compound

HRID 1581688Notes

Reaction equation

HRID 1581688 reaction equation
C(Cl)CCl.[C:5]1([CH3:14])[C:6]([C:11]([OH:13])=O)=[CH:7][CH:8]=[CH:9][CH:10]=1.[CH3:15][N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17]1[CH2:25][NH:26][CH3:27].C1C=CC2N(O)N=NC=2C=1.O>CN(C=O)C>[CH3:27][N:26]([CH2:25][C:17]1[N:16]([CH3:15])[C:24]2[C:19]([CH:18]=1)=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:11](=[O:13])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH3:14]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 962WaterHCID 83732-Methylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amine

Product 1

HCID 12125396HCID 12125396, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (0.22 g, 1.15 mmole) was added to a solution of ortho-toluic acid (0.15 g, 1.10 mmole), 1-methyl-2-(methylaminomethyl)indole (0.20 g, 1.15 mmole), and HOBt.H2O (0.15 g, 1.11 mmole) in DMF 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 and dried over MgSO4. Flash chromatography on silica gel (20% EtOAc/hexanes) gave a colorless gum, which was triturated with Et2O to afford the title compound (0.2 g, 37%) as a white solid: 1H NMR (300 MHz, CDCl3) indicated an approximately 5:1 mixture of amide rotamers; for the major rotamer: δ 7.60 (d, J=7.7 Hz, 1H), 7.05-7.40 (m, 7H), 6.52 (s, 1H), 5.01 (s, 2H), 3.85 (s, 3H), 2.71 (s, 3H), 2.30 (s, 3H); for the minor rotamer: δ 7.60 (d, J=7.7 Hz, 1H), 7.05-7.40 (m, 7H), 6.44 (s, 1H), 4.52 (s, 2H), 3.50 (s, 3H), 3.14 (s, 3H), 2.37 (s, 3H); MS (ES) m/e 293 (M+H)+. Anal. Calcd for C19H20N2O.0.35H2O: C, 76.40; H, 6.99; N, 9.38. Found: C, 76.10; H, 6.83; N, 9.33.

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
  6. dry with materialdried over MgSO4
  7. customFlash chromatography on silica gel (20% EtOAc/hexanes) gave a colorless gum, which
  8. customwas triturated with Et2O

Sources & evidence

ORD record
ord-6706605fadad46308e893913d28f75ed
Source dataset
uspto-grants-2004_05
Patent number
US06730684B1

Reaction notes

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