Tert-butyl 3-fluoro-4-(thiazol-4-yl)phenylcarbamate → 3-Fluoro-4-(thiazol-4-yl)benzenamine

HRID 1802006Notes

Reaction equation

HRID 1802006 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:13]C(=O)OC(C)(C)C)[CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[CH:10][S:11][CH:12]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[C:4]([NH2:13])[CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[CH:10][S:11][CH:12]=1

Participants

4

Reactant 1

HCID 57471879Tert-butyl 3-fluoro-4-(thiazol-4-yl)phenylcarbamate

Product 1

HCID 574718803-Fluoro-4-(thiazol-4-yl)benzenamineYield 81.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 3-fluoro-4-(thiazol-4-yl)phenylcarbamate (270 mg, 0.92 mmol) in CH2Cl2 (2 mL) and TFA (4 mL) was stirred at room temperature for 60 min. It was then concentrated in vacuo. The residue was dissolved in CH2Cl2 (20 mL), which was washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 3-fluoro-4-(thiazol-4-yl)benzenamine (145 mg) as free base. MS195.2 (M+H)

Workup

  1. concentrationIt was then concentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  3. washwhich was washed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be799e093b0643fc8390efa9b1b49f63
Source dataset
uspto-grants-2013_01
Patent number
US08349860B2

Reaction notes

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