Trifluoroacetic acid → HCID 58459388, compound

HRID 2036562Notes

Reaction equation

HRID 2036562 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([Cl:11])[C:5]2=[N:4][C:3]=1[CH2:12][N:13]1C(=O)C2C(=CC=CC=2)C1=O.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(=O)NC(=O)C2=CC=CC=C12.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:11][C:10]1[C:5]2[N:6]([C:2]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:3]([CH2:12][NH2:13])[N:4]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 6809PhthalimideHCID 66827Phenylboronic AcidHCID 58459111HCID 58459111, compound

Product 1

HCID 58459388HCID 58459388, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-((3-Bromo-8-chloroimidazo[1,2-a]pyridin-2-yl)methyl)isoindoline-1,3-dione was coupled with phenyl boronic acid according to Step C3b in General Procedure C. Partial hydrolysis of the phthalimide was observed under the reaction conditions. The crude intermediate was treated with DCM and TFA for a week. The reaction mixture was concentrated under reduced pressure and purified by reverse phase semi-prep HPLC. The fractions containing the desired product were lyophilized. The lyophilate was partitioned with satd. aq. NaHCO3 solution and EtOAc. The aq. layer was extracted three times with EtOAc. The combined organic layers were dried with Na2SO4, filtered, and concentrated under reduced pressure to give (8-chloro-3-phenylimidazo[1,2-a]pyridin-2-yl)methanamine.

Workup

  1. customwas observed under the reaction conditions
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by reverse phase semi-prep HPLC
  4. additionThe fractions containing the desired product
  5. customThe lyophilate was partitioned with satd
  6. extractionThe aq. layer was extracted three times with EtOAc
  7. dry with materialThe combined organic layers were dried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0987bdc2264f43d58ae48ae63d93aff7
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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