Dimethylformamide → HCID 136373299, compound

HRID 1802754Notes

Reaction equation

HRID 1802754 reaction equation
O=P(Cl)(Cl)Cl.[CH3:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=1.CN(C)[CH:23]=[O:24]>>[CH3:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[NH:13][C:14]3[C:19]([C:20]=2[CH:23]=[O:24])=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 136373300HCID 136373300, compound

Product 1

HCID 136373299HCID 136373299, compound

Procedure

With vigorous stirring, POCl3 (1.4 mL, 15 mmol) was added slowly to dimethylformamide (2 mL) at 0° C. 2-(5-Methyl-isoxazol-3-yl)-1H-indole (1.0 g, 5.04 mmol) dissolved in N,N-dimethylformamide (8 mL) was added. The reaction mixture was allowed to come to room temperature, stirred for 4 h, and quenched with ice cold water followed by a 10% sodium hydroxide solution. The resulting precipitate was washed with water, dried in vacuo, and purified via silica gel column chromatography (30% ethyl acetate in petroleum ether) to obtain 2-(5-methyl-isoxazol-3-yl)-1H-indole-3-carbaldehyde (0.6 g, 2.65 mmol) as a white solid.

Workup

  1. additionwas added
  2. customto come to room temperature
  3. customquenched with ice cold water
  4. washThe resulting precipitate was washed with water
  5. customdried in vacuo
  6. custompurified via silica gel column chromatography (30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-8881343340bd447b8dd79ba78df5c716
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

Loading…