Dimethylformamide → HCID 86034612, compound

HRID 1297271Notes

Reaction equation

HRID 1297271 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16]1[CH:21]=[CH:20][C:19]([O:22]COC)=[CH:18][CH:17]=1)[C:11]([CH3:26])=[CH:10]2.CN(C)[CH:29]=[O:30]>>[Cl:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:11]([CH3:26])=[C:10]2[CH:29]=[O:30]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 69299361HCID 69299361, compound

Product 1

HCID 86034612HCID 86034612, compoundYield 85%

Procedure

Phosphorous oxychloride (5 mL) was added to anhydrous dimethylformamide (10 mL) and stirred at room temperature for 15 min whereupon a solution of 5-chloro-1-(4-methoxymethyloxyphenyl)-2-methyl-1H-indole (1.22 g, 3.5 mmol) in dimethylformamide (10 mL) was added. The solution was reacted according to the procedure used in Example 2a to afford a tan solid (85%): mp>240° C.; 1H NMR (DMSO-d6): δ 2.52 (3H, s), 6.97-7.02 (3H, m), 7.22 (1H, dd, J=2.3 Hz, J=8.7 Hz), 7.30 (2H, d, J=8.6 Hz), 8.40 (1H, d, J=2.1 Hz), 10.02 (1H, s), 10.16 (1H, s); MS m/Z (M+H)+ 286/288 (1 Cl).

Workup

  1. additionwas added
  2. customThe solution was reacted

Sources & evidence

ORD record
ord-4860da067c3946f18bff1e03ef9a979d
Source dataset
uspto-grants-2007_07
Patent number
US07250440B2

Reaction notes

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