Phosphorus oxychloride → HCID 86681528, compound

HRID 2361415Notes

Reaction equation

HRID 2361415 reaction equation
[C:1]([C:3]1[C:8]2[NH:9][C:10]3[CH:11]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:14][C:15]=3[C:7]=2[C:6](=O)[NH:5][CH:4]=1)#[N:2].P(Cl)(Cl)([Cl:23])=O>O1CCOCC1>[CH3:19][O:18][C:16]([C:12]1[CH:13]=[CH:14][C:15]2[C:7]3[C:6]([Cl:23])=[N:5][CH:4]=[C:3]([C:1]#[N:2])[C:8]=3[NH:9][C:10]=2[CH:11]=1)=[O:17]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67995457HCID 67995457, compound

Product 1

HCID 86681528HCID 86681528, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
93 °C

Procedure

A stirred slurry of methyl 4-cyano-1-oxo-2,5-dihydro-1H-pyrido[4,3-b]indole-7-carboxylate (1.000 g, 3.74 mmol) in Dioxane (Volume: 25 mL) was heated to 93° C. Phosphorus oxychloride (1.713 mL, 18.71 mmol) was added slowly dropwise over 30 minutes. After complete addition the reaction mixture was stirred at 93° C. for 5 hours then at room temperature overnight. LC-MS showed complete conversion to the desired product mass with minor by-products. The reaction mixture was diluted with 25 ml ethyl acetate and filtered. The filtrate was concentrated under vacuum to give 1.311 g crude solid tan product. The crude product was washed with diethyl ether, then triturated with acetonitrile and filtered to give Methyl-1-chloro-4-cyano-5H-pyrido[4,3-b]indole-7-carboxylate as a tan solid [0.855 g, 2.99 mmol, 80% yield]. The product had an HPLC Retention Time=3.658 min [4 min grad, 10% MeOH/water to 90% MeOH/water, 0.1% TFA, YMC COMBISCREEN® ODS-A, 4.6×50 mm, 220 nM]; LC/MS+1 286.1

Workup

  1. additionAfter complete addition the reaction mixture
  2. customat room temperature
  3. customovernight

Sources & evidence

ORD record
ord-aadf9ca5920f4f8f8632b2e5f9c83dad
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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