Dimethylformamide → HCID 84682738, compound

HRID 2174502Notes

Reaction equation

HRID 2174502 reaction equation
P(Cl)(Cl)(Cl)=O.[CH:6]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=2)([CH3:8])[CH3:7].CN(C)[CH:22]=[O:23]>>[CH:6]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[CH:22]=[O:23])=[CH:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=2)([CH3:8])[CH3:7]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 10465109HCID 10465109, compound

Product 1

HCID 84682738HCID 84682738, compoundYield 86%

Procedure

Dimethylformamide (2 mL) was cooled to 0° C. Phosphorus oxychloride (0.5 mL) was added and the reaction mixture was stirred for 10 minutes. A solution of 2-isopropyl-5-methoxyindole (200 mg, 1.05 mmol) in dimethylformamide (3 mL) was added to the reaction mixture dropwise over 10 minutes. The solution was stirred for an additional 40 minutes. The reaction mixture was added to ice cold 1 N NaOH (50 mL) and stirred for 10 minutes. The precipitate was collected and dried overnight in an oil driven vacuum pump equipped to a vacuum desiccator set at 40° C. yielding a light brown solid (318 mg, 86%): TLC Rf 0.71 in 4:1 ethyl acetate/hexanes. Melting point=181-183° C. 1H NMR (600 MHz, CDCl3) δ 10.22 (s, 1H), 8.63 (s, 1H), 7.79 (d, 1H, J=2.46 Hz), 7.26-7.24 (d, 1H, J=8.94 Hz), 6.89-6.87 (dd, 1H, J1=2.52 Hz, J2=8.76 Hz), 3.87 (s, 3H), 3.79-3.74 (m, 1H), 1.46-1.45 (d, 6H, J=7.02 Hz); 13C NMR (150 MHz, CDCl3) δ 184.1, 156.52, 156.51, 129.4, 126.9, 113.5, 113.2, 111.6, 103.0, 55.8, 25.8, 22.7. Elemental analysis calculated for C13H15NO2: C, 71.87; H, 6.96; N, 6.45. Found: C, 71.59; H, 6.98; N, 6.39.

Workup

  1. stirringThe solution was stirred for an additional 40 minutes
  2. stirringstirred for 10 minutes
  3. customThe precipitate was collected
  4. customdried overnight in an oil
  5. customequipped to a vacuum desiccator
  6. customset at 40° C.

Sources & evidence

ORD record
ord-98a704a88b2c4453aafb1a11d0324bd6
Source dataset
uspto-grants-2015_06
Patent number
US09061994B1

Reaction notes

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