Trifluoroacetic acid → HCID 178525019, compound

HRID 1527257Notes

Reaction equation

HRID 1527257 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH:15]=2)[C:10]([Br:27])=[N:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:20]([O:19][C:17]([C:14]1[CH:15]=[C:16]2[C:11]([C:10]([Br:27])=[N:9][NH:8]2)=[CH:12][CH:13]=1)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68283041HCID 68283041, compound

Product 1

HCID 178525019HCID 178525019, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-indazole-1,6-dicarboxylic acid 6-benzyl ester 1-tert-butyl ester (2.05 g, 4.75 mmol) and TFA (3.66 mL, 47.5 mmol) in CH2Cl2 (30 mL) was stirred at RT for 16 h. A saturated aqueous solution of NaHCO3 was added, the layers were separated and the aqueous layer was extracted with CH2Cl2 (×3). The combined organic extracts were dried (Na2SO4), filtered and concentrated and the material thus obtained was used without further purification in the next step. MS (UPLC/MS): 331.2/333.2 [M+H]+, 329.3/331.2 [M−H]−; tR (UPLC conditions m): 1.18 min.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (×3)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe material thus obtained
  7. customwas used without further purification in the next step
  8. custom1.18 min.

Sources & evidence

ORD record
ord-51f9d1ce1f284cb2bb5e3bb5688447bf
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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