Boron tribromide → 1-[4-(2-Fluorophenyl)-1,3-thiazol-2-yl]piperazine

HRID 1361475Notes

Reaction equation

HRID 1361475 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([N:13]2[CH2:18][CH2:17][N:16](C(OCC3C=CC=CC=3)=O)[CH2:15][CH2:14]2)[S:11][CH:12]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([N:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)[S:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15984569Benzyl 4-(4-(2-fluorophenyl)thiazol-2-yl)piperazine-1-carboxylate

Product 1

HCID 581827331-[4-(2-Fluorophenyl)-1,3-thiazol-2-yl]piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-50 °C

Procedure

To a solution of benzyl 4-(4-(2-fluorophenyl)thiazol-2-yl)piperazine-1-carboxylate (0.85 g, 2.1 mmol) in CH2Cl2 (2 μL) cooled to −50° C. was added boron tribromide (1 M in CH2Cl2, 8.6 mL, 8.6 mmol). The reaction was stirred at −50° C. for 20 min and then carefully quenched with saturated aqueous NaHCO3. The mixture was extracted with CH2Cl2, and the combined extracts were washed with water, dried over Na2SO4, and concentrated under reduced pressure to yield 1-(4-(2-fluorophenyl)thiazol-2-yl)piperazine. LC/MS: m/z 264.1 (M+H)+ at 2.04 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customcarefully quenched with saturated aqueous NaHCO3
  2. extractionThe mixture was extracted with CH2Cl2
  3. washthe combined extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f60637d4abd47f99a648cf971372941
Source dataset
uspto-grants-2011_02
Patent number
US07880008B2

Reaction notes

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