Boron tribromide → HCID 178519905, compound

HRID 579466Notes

Reaction equation

HRID 579466 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][S:6][C:7]1[NH:11][C:10]2[C:12]([CH:18]=[O:19])=[C:13]([O:16]C)[CH:14]=[CH:15][C:9]=2[N:8]=1)C.B(Br)(Br)Br>ClCCl>[CH:18]([C:12]1[C:10]2[NH:11][C:7]([S:6][CH2:5][C:4]([OH:20])=[O:3])=[N:8][C:9]=2[CH:15]=[CH:14][C:13]=1[OH:16])=[O:19]

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 178473165HCID 178473165, compound

Product 1

HCID 178519905HCID 178519905, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (7-Formyl-6-methoxy-1H-benzoimidazol-2-ylsulfanyl)-acetic acid ethyl ester (500 mg, 1.88 mmol) in abs. dichloromethane (40 mL) stirred under argon at −78° C., boron tribromide (723 μl, 1.88 g, 7.52 mmol) was added dropwise and the mixture was warmed to room temperature and stirred for 2 h. An additional portion of boron tribromide (723 μl, 1.88 g, 7.52 mmol) was added at −78° C. and stirred for 2 h at room temperature. The mixture was quenched by slow addition of 120 mL. of water. The mixture was evaporated to dryness, suspended in boiling ethyl acetate, and the solid was filtered off. The filtrate was evaporated and triturated with diethyl ether. The title compound (220 mg, 0.87 mmol, 46%) was obtained as a light orange powder.

Workup

  1. stirringstirred for 2 h at room temperature
  2. customThe mixture was quenched by slow addition of 120 mL
  3. customThe mixture was evaporated to dryness
  4. filtrationthe solid was filtered off
  5. customThe filtrate was evaporated
  6. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-33f5a0b16059401ca9c15bcc9c87fce1
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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