Hydrochloric Acid → (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)(2,6-dichloro-3-fluorophenyl)methanol

HRID 2046907Notes

Reaction equation

HRID 2046907 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[Cl:11][C:12]1[C:19]([F:20])=[CH:18][CH:17]=[C:16]([Cl:21])[C:13]=1[CH:14]=[O:15].[OH-].[K+].Cl>CO.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:14]([C:13]3[C:16]([Cl:21])=[CH:17][CH:18]=[C:19]([F:20])[C:12]=3[Cl:11])[OH:15])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 189456742,6-Dichloro-3-fluorobenzaldehyde

Product 1

HCID 67004517(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)(2,6-dichloro-3-fluorophenyl)methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine (0.100 g, 0.508 mmol) and 2,6-dichloro-3-fluorobenzaldehyde (0.107 g, 0.558 mmol) in MeOH (5 mL) was added potassium hydroxide (0.199 g, 3.553 mmol) at 0° C. under nitrogen atmosphere. The resulting mixture was then stirred at r.t. overnight. The mixture was then poured into water (50 mL), acidified with 2N HCl and extracted with ethyl acetate (50 mL×3). The organics were combined, dried (Na2SO4) and concentrated under reduced pressure to give a crude residue which was then purified by chromatography (eluent: 20% ethyl acetate in hexane). MS (ES+): m/z=388.85, 390.84, 392.83 [MH+]. HPLC: tR=3.29 min (ZQ3, polar—5 min).

Workup

  1. extractionextracted with ethyl acetate (50 mL×3)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fe54e913d9314131bedbbef8965b66f1
Source dataset
uspto-grants-2013_11
Patent number
US08592448B2

Reaction notes

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