Potassium Phosphate, Tribasic → Methyl 4-Fluoro-2-{1H-pyrrolo[2,3-b]pyridin-5-yloxy}benzoate

HRID 1468980Notes

Reaction equation

HRID 1468980 reaction equation
C([Si](C(C)C)(C(C)C)[N:5]1[C:9]2=[N:10][CH:11]=[C:12]([OH:14])[CH:13]=[C:8]2[CH:7]=[CH:6]1)(C)C.F[C:22]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOCCOC.CCOCC>[NH:5]1[C:9]2=[N:10][CH:11]=[C:12]([O:14][C:22]3[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:23]=3[C:24]([O:26][CH3:27])=[O:25])[CH:13]=[C:8]2[CH:7]=[CH:6]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2782897Methyl 2,4-DifluorobenzoateHCID 49758888HCID 49758888, compound

Product 1

HCID 66713127Methyl 4-Fluoro-2-{1H-pyrrolo[2,3-b]pyridin-5-yloxy}benzoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8150DiglymeSolvent

Procedure

A mixture of EXAMPLE 1G (8.5 g), methyl 2,4-difluorobenzoate (7.05 g), and K3PO4 (9.32 g) in diglyme (40 mL) at 115° C was stirred for 24 hours. The reaction was cooled, diluted with ether (600 mL), and washed twice with water, and brine, and concentrated. The residue was purified by flash chomatography, eluting with 2-50% ethyl acetate in hexanes to provide the title compound.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed twice with water, and brine
  3. concentrationconcentrated
  4. customThe residue was purified by flash chomatography
  5. washeluting with 2-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-bdc85461ecf24ba18f0e9d4d8a96ec0f
Source dataset
uspto-grants-2015_04
Patent number
US09006247B2

Reaction notes

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