Dimethylformamide → HCID 22663386, compound

HRID 392192Notes

Reaction equation

HRID 392192 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([Cl:25])[C:12]=1[NH:13][C:14]([C:16]1[CH:24]=[C:23]2[C:19]([CH:20]=[CH:21][NH:22]2)=[CH:18][CH:17]=1)=[O:15].CN(C)[CH:28]=[O:29]>>[Cl:25][C:11]1[CH:10]=[N:9][CH:8]=[C:7]([Cl:6])[C:12]=1[NH:13][C:14]([C:16]1[CH:24]=[C:23]2[C:19]([C:20]([CH:28]=[O:29])=[CH:21][NH:22]2)=[CH:18][CH:17]=1)=[O:15]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 22663173HCID 22663173, compound

Product 1

HCID 22663386HCID 22663386, compound

Conditions

Temperature
0 °C

Procedure

A stirred solution of dimethylformamide (10 ml), under nitrogen and at 0° C., was treated with phosphorus oxychloride (0.6 ml). After stirring for 30 minutes at 0° C. the mixture was treated with a solution of N-(3,5-dichloro-pyridin-4-yl)-1H-indole-6-carboxamide [1.55 g, Example 1(bg)] in dimethylformamide (5 ml). The mixture was then heated at 40° C. for 45 minutes then cooled to room temperature and then partitioned between ethyl acetate (25 ml) and saturated sodium bicarbonate (50 ml). The organic layer was washed with water (75 ml) then dried over sodium sulphate then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2, v/v) to yield the title compound (0.53 g) as a white solid. [Elemental analysis:— C, 53.83; H, 2.99; N, 12.31%. Calculated for C15H9Cl2N3O2:— C, 53.92; H, 2.71; N, 12.57%].

Workup

  1. temperatureThe mixture was then heated at 40° C. for 45 minutes
  2. temperaturethen cooled to room temperature
  3. custompartitioned between ethyl acetate (25 ml) and saturated sodium bicarbonate (50 ml)
  4. washThe organic layer was washed with water (75 ml)
  5. dry with materialthen dried over sodium sulphate
  6. customthen evaporated
  7. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2

Sources & evidence

ORD record
ord-67564490aa864d6cbabb8308d1cc44e7
Source dataset
uspto-grants-2004_10
Patent number
US06800645B1

Reaction notes

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