Dimethylformamide → HCID 86597102, compound

HRID 1297270Notes

Reaction equation

HRID 1297270 reaction equation
P(Cl)(Cl)(Cl)=O.[F: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][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:18][CH:17]=1)[C:11]([CH3:30])=[CH:10]2.CN(C)[CH:33]=[O:34]>>[F:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:20][CH:21]=1)[C:11]([CH3:30])=[C:10]2[CH:33]=[O:34]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 69299373HCID 69299373, compound

Product 1

HCID 86597102HCID 86597102, compoundYield 85%

Procedure

Phosphorous oxychloride (5 mL) was added to anhydrous dimethylformamide (10 mL) and the mixture allowed to stir at room temperature for 15 min whereupon a solution of 5-fluoro-1-(4-benzyloxyphenyl)-2-methyl-1H-indole (1.63 g, 4.9 mmol) in dimethylformamide (10 mL) was added and reacted according to the procedure used in Example 2a to afford a tan solid (85%): mp 219-220° C.; 1H NMR (DMSO-d6): δ 2.53 (3H, s), 5.22 (2H, s), 6.99-7.06 (2H, m), 7.27 (2H, d, J=8.9 Hz), 7.37-7.53 (7H, m), 7.86 (1H, dd, J=2.5 Hz, J=9.5 Hz); MS m/z (M+H)+ 360. Anal. for C23H18FNO2·0.5H2O: Calc'd: C, 74.99; H, 5.20; N, 3.80. Found: C, 74.91; H, 4.96; N, 3.59.

Workup

  1. additionwas added
  2. customreacted

Sources & evidence

ORD record
ord-17e8ccf3e0424594a06553e5b0dd1452
Source dataset
uspto-grants-2007_07
Patent number
US07250440B2

Reaction notes

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