Dimethylformamide → HCID 136373299, compound

HRID 549381Notes

Reaction equation

HRID 549381 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-acdaab784eed43c3adbfe42624a4789c
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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