Hydrochloric Acid → HCID 70652010, compound

HRID 2361437Notes

Reaction equation

HRID 2361437 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[NH2:12])=[C:7]2[C:3]=1[C:4]1[CH:17]=[C:16](C(OCC)=O)[N:15]=[CH:14][C:5]=1[NH:6]2.Cl.[C:24]([O-])(O)=O.[Na+].[CH2:29]1[CH2:33][O:32]CC1>CCOCC>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([NH2:12])=[O:13])=[C:7]2[C:3]=1[C:4]1[CH:17]=[C:16]([C:33]([OH:32])([CH3:29])[CH3:24])[N:15]=[CH:14][C:5]=1[NH:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 67995021HCID 67995021, compound

Product 1

HCID 70652010HCID 70652010, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of ethyl 5-bromo-8-carbamoyl-9H-pyrido[3,4-b]indole-3-carboxylate (0.4 g, 1.104 mmol) in THF (31.6 mL) was cooled in a salt-ice bath slowly treated with methylithium (1.6 M in ether, 3.80 mL, 6.07 mmol). The solution was stirred at −5° C. for 1.5 h, then was treated with ice and 1 M aqueous HCl (7 mL). The mixture was made basic with NaHCO3 (aq) and extracted with chloroform-isopropanol (3:1). The organic phase was washed with brine, dried and concentrated. The residue was subjected to column chromatography on silica gel (40 g), eluting with Methanol-CH2Cl2 (gradient from 2:98 to 10:90) to provide the desired product as a yellow solid (128 mg, 33% yield). LCMS (M+H)+ m/z 347.9, 349.9.

Workup

  1. extractionextracted with chloroform-isopropanol (3:1)
  2. washThe organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. washeluting with Methanol-CH2Cl2 (gradient from 2:98 to 10:90)

Sources & evidence

ORD record
ord-92496f0052324b7a92e883431672794e
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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