Boron tribromide → HCID 59853453, compound

HRID 2374222Notes

Reaction equation

HRID 2374222 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([CH2:25][OH:26])[N:7]([CH2:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[C:8]=1[S:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16]C)[CH:11]=1)([CH3:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[OH:26][CH2:25][C:6]1[N:7]([CH2:18][C:19]2[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=2)[C:8]([S:9][C:10]2[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=2)=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59853488HCID 59853488, compound

Product 1

HCID 59853453HCID 59853453, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of alcohol 38 (56 mg, 0.15 mmol) in CH2Cl2 (2 mL) was added 1M BBr3 in CH2Cl2 at 0° C. See Scheme 22 (FIG. 24). After the reaction mixture was stirred for 1 h at 0° C., the mixture was partitioned between CH2Cl2 and sat. NaHCO3. The aqueous phase was neutralized with solid NaHCO3 and extracted with CH2Cl2 and EtOAc. The organic phase was dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude product was chromatographed on silica gel (eluting 5-10% MeOH/CH2Cl2) to give 3-(2-hydroxymethyl-5-isopropyl-3-pyridin-4-ylmethyl-3H-imidazol-4-ylsulfanyl)-phenol 39 (43 mg, 81%) as a colorless solid.

Workup

  1. customthe mixture was partitioned between CH2Cl2 and sat. NaHCO3
  2. extractionextracted with CH2Cl2 and EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude product was chromatographed on silica gel (eluting 5-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-19fc43eac5a049fc8587338a479e5ea5
Source dataset
uspto-grants-2008_12
Patent number
US07462608B2

Reaction notes

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