Hydrochloric Acid → HCID 68576167, compound

HRID 33941Notes

Reaction equation

HRID 33941 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[CH:16][N:15]=[C:14]2[CH3:24])=[CH:9][CH:8]=1.[OH-].[Na+].Cl>C(Cl)Cl>[CH3:24][C:14]1[N:13]([C:10]2[CH:11]=[CH:12][C:7]([OH:6])=[CH:8][CH:9]=2)[C:17]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 66896785HCID 66896785, compound

Product 1

HCID 68576167HCID 68576167, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of boron tribromide (1 M in methylene chloride, 2.1 mL, 2.1 mmol) was added dropwise to a solution of Preparation 82 (4-(1-(4-methoxyphenyl)-2-methyl-1H-imidazol-5-yl)pyridine, 220 mg, 0.83 mmol) in methylene chloride (5 mL) at 0° C. After stirring at 23° C. for 24 h, aqueous sodium hydroxide solution (1 N, 15 mL) was added and the mixture was stirred at 23° C. for 1 h. The pH was adjusted to 7 by the addition of aqueous hydrochloric acid (1N), the mixture was extracted with methylene chloride/isopropanol (4:1, 3×30 mL), the combined organic layers were dried (MgSO4), were filtered, and were concentrated in vacuo. The residue was purified by silica gel chromatography using chloroform-methanol (20:1 to 10:1) to afford 150 mg (72% yield ) of the title compound; diagnostic 13C NMR signals (100 MHz, CDCl3) δ 159.337, 149.548, 149.302, 138.302, 131.131, 128.760, 128.170, 127.310, 121.163, 117.237, 13.881; MS (AP/Cl) 252.4 (M+H)+.

Workup

  1. stirringthe mixture was stirred at 23° C. for 1 h
  2. extractionthe mixture was extracted with methylene chloride/isopropanol (4:1, 3×30 mL)
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. filtrationwere filtered
  5. concentrationwere concentrated in vacuo
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-74103aceaf5a4990827b91415ab8de27
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

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