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

HRID 2168075Notes

Reaction equation

HRID 2168075 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 277G (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 crude product was chromatographed on silica gel with 2-50% ethyl acetate/hexanes.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed twice with water, and brine
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel with 2-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-150461156a9a490b881de9d5dfd3c62c
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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