Fluorobenzene → HCID 86659800, compound

HRID 1404602Notes

Reaction equation

HRID 1404602 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:19]([O-:21])=O)[C:5]([CH:8]([C:14](OCC)=O)C(OCC)=O)=[N:6][CH:7]=1.F[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[N:19]([O:21][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:14][CH:8]=[C:5]2[NH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10008FluorobenzeneHCID 11430Potassium CarbonateHCID 57516275Diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate

Product 1

HCID 86659800HCID 86659800, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-bromo-1H-pyrrolo[3,2-b]pyridin-1-ol (prepared as in Example 1: 200 mg, 1.0 mmol, 1.0 eq), fluorobenzene (485 mg, 5.0 mmol, 5.0 eq), and K2CO3 (690 mg, 5.0 mmol, 5.0 eq) in 2 ml of DMF were microwaved (160° C.) for 30 min. The reaction mixture was allowed to cool to room temperature, the solvent was evaporated, and the mixture was chromatographed (MeOH/DCM 1:20) to give a light yellow solid, 110 mg, in 50% yield.

Workup

  1. customthe solvent was evaporated
  2. customthe mixture was chromatographed (MeOH/DCM 1:20)
  3. customto give a light yellow solid, 110 mg

Sources & evidence

ORD record
ord-99ff9e6cb67645cab5181e47314be2dc
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

Loading…