Boron tribromide → HCID 25015016, compound

HRID 501063Notes

Reaction equation

HRID 501063 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[C:14]([F:15])=[CH:13][C:12]([C:16]2[O:17][C:18]3[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][C:19]=3[CH:20]=2)=[CH:11][N:10]=1)C)(C)(C)C.B(Br)(Br)Br>C(Cl)Cl>[F:15][C:14]1[CH:13]=[C:12]([C:16]2[O:17][C:18]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:19]=3[CH:20]=2)[CH:11]=[N:10][C:9]=1[NH:7][CH3:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59424800HCID 59424800, compound

Product 1

HCID 25015016HCID 25015016, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-fluoro-5-(5-methoxy-benzofuran-2-yl)-pyridin-2-yl]-methyl-carbamic acid tert-butyl ester (130 mg, 0.35 mmol) in dry CH2Cl2 (400 mL), BBr3 (2.1 mL, 2.10 mmol) was added at −78° C. The reaction mixture was allowed to warm to room temperature and the stirring was continued for 14 hours. The reaction was then quenched by addition of saturated aqueous NaHCO3 and the product was extracted with EtOAc (3×30 mL). The combined extracts were dried over MgSO4 and concentrated in vacuo. The crude residue was purified by preparative TLC using 30% EtOAc in CH2Cl2 to afford 2-(5-fluoro-6-methylamino-pyridin-3-yl)-benzofuran-5-ol (37 mg) as a white solid.

Workup

  1. customThe reaction was then quenched by addition of saturated aqueous NaHCO3
  2. extractionthe product was extracted with EtOAc (3×30 mL)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by preparative TLC

Sources & evidence

ORD record
ord-1b33c13a6a6f407eb0afc1808597d1a3
Source dataset
uspto-grants-2010_08
Patent number
US07772256B2

Reaction notes

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