Dimethylformamide → HCID 86034609, compound

HRID 1297269Notes

Reaction equation

HRID 1297269 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[C:21]2[CH3:29])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].CN(C)[CH:34]=[O:35]>>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([CH:34]=[O:35])=[C:21]2[CH3:29])=[CH:16][CH:15]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 69301089HCID 69301089, compound

Product 1

HCID 86034609HCID 86034609, compound

Procedure

Phosphorous oxychloride (3 mL) was added to anhydrous dimethylformamide (6 mL) and the mixture was stirred at room temperature for 15 min. A mixture of 1-(4-benzyloxyphenyl)-2-methyl-1H-indole (0.94 g, 3 mmol) in dimethylformamide (10 mL) was added and the mixture heated to 80° C. for 18 hr. The reaction mixture was poured onto ice and adjusted to a pH of 7 by the addition of 2 N NaOH. The mixture was extracted with ethyl acetate (2×100 mL). The organic layer washed with water and brine and dried over MgSO4. Evaporation to provide the product as a dark solid. Purification by silica gel chromatography (10% EtOAC-hexanes) provided a white solid (63%): mp 150-152° C.; 1H NMR (DMSO-d6): δ 2.54 (3H, s), 5.22 (2H, s), 6.99 (1H, d, J=7.9 Hz), 7.17-7.42 (4H, m), 7.45-7.54 (7H, m), 8.17 (1H, d, J=7.5 Hz), 10.19 (1H, s); MS m/z (M+H)+ 342. Anal. for C23H19NO2: Calc'd: C, 80.92; H, 5.61; N, 4.10. Found: C, 80.76; H, 5.70; N, 3.93.

Workup

  1. additionwas added
  2. temperaturethe mixture heated to 80° C. for 18 hr
  3. additionThe reaction mixture was poured onto ice
  4. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  5. washThe organic layer washed with water and brine
  6. dry with materialdried over MgSO4
  7. customEvaporation

Sources & evidence

ORD record
ord-8691cc51218a4bcc9433d1a99becee1f
Source dataset
uspto-grants-2007_07
Patent number
US07250440B2

Reaction notes

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