Phosphorus oxychloride → HCID 59447943, compound

HRID 1480742Notes

Reaction equation

HRID 1480742 reaction equation
O[C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:5]=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178497210HCID 178497210, compound

Product 1

HCID 59447943HCID 59447943, compoundYield 30.6%

Conditions

Temperature
90 °C

Procedure

In a 100 mL round-bottom flask a mixture of methyl 4-hydroxy-9H-pyrimido[4,5-b]indole-7-carboxylate (1.1 g, 4.5 mmol) and phosphorous oxychloride (15 mL, 161 mmol) was heated to 90° C. for 16 hours, cooled down to room temperature and evaporated under reduced pressure. The residue was suspended in dichloromethane (20 mL) and filtered through Celite. Evaporation afforded the title compound as an orange solid (360 mg). LCMS m/z 262.0 (M+H)+, retention time (on analytical HPLC)=2.02 minutes.

Workup

  1. temperaturecooled down to room temperature
  2. customevaporated under reduced pressure
  3. filtrationfiltered through Celite
  4. customEvaporation

Sources & evidence

ORD record
ord-56eb1a1a9ee64e1fba559803bbc23ad6
Source dataset
uspto-grants-2016_08
Patent number
US09409906B2

Reaction notes

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