Trifluoroacetic acid → HCID 71621298, compound

HRID 1473890Notes

Reaction equation

HRID 1473890 reaction equation
[CH:1]([C:3]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:4]=1[O:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[N:10][N:11]2C(OC(C)(C)C)=O)=[O:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:11]1[C:12]2[C:8](=[C:7]([CH2:6][O:5][C:4]3[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:3]=3[CH:1]=[O:2])[CH:15]=[CH:14][CH:13]=2)[CH:9]=[N:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86690717HCID 86690717, compound

Product 1

HCID 71621298HCID 71621298, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 4-((2-formyl-4-methoxyphenoxy)methyl)-1H-indazole-1-carboxylate (88 mg, 0.23 mmol) in DCM (5.0 mL) was added TFA (2.0 mL). The mixture was stirred at rt for 2 h and concentrated. The crude was purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 2-((1H-indazol-4-yl)methoxy)-5-methoxybenzaldehyde (50 mg, 77%) as a white solid. 1H NMR (400 MHz; CDCl3) δ=10.53 (s, 1H), 8.23 (s, 1H), 7.54 (d, 1H) 7.43 (t, 1H), 7.38 (d, 1H), 7.25 (d, 1H), 7.08-7.15 (m, 2H), 5.51 (s, 2H), 3.82 (s, 3H). LRMS (M+H+) m/z 283.1.

Workup

  1. concentrationconcentrated
  2. customThe crude was purified on silica gel using
  3. additiona mixture of EtOAc and hexanes as eluent

Sources & evidence

ORD record
ord-865f8bdce8084ccdaa9209a6172a256d
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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