Boron tribromide → HCID 12150668, compound

HRID 2086149Notes

Reaction equation

HRID 2086149 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:28])[C:7]2[C:12]([CH:13]=1)=[C:11]([Cl:14])[C:10]([O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22]C)=[C:18]([CH:24]([CH3:26])[CH3:25])[CH:17]=1)=[C:9]([Cl:27])[CH:8]=2)=[O:4].B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:28])[C:7]2[C:12]([CH:13]=1)=[C:11]([Cl:14])[C:10]([O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH:24]([CH3:25])[CH3:26])[CH:17]=1)=[C:9]([Cl:27])[CH:8]=2)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 12150667HCID 12150667, compound

Product 1

HCID 12150668HCID 12150668, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4,6-dichloro-5-(3-isopropyl-4-methoxy-phenoxy)-1-methyl-1H-indole-2-carboxylic acid methyl ester (46 mg, 0.11 mmol) in dry methylene chloride (1 mL) at room temperature was added boron tribromide (1M in methylene chloride, 0.22 mL, 0.22 mmol). After stirring at room temperature for 1.5 hours, the reaction was quenched with methanol (0.5 mL), stirred for 15 minutes, then diluted with water (10 mL), and stirred for another 15 minutes. The solution was extracted with methylene chloride (3 times 5 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated. The residue was purified by preparative thin layer chromatography (3% methanol in methylene chloride) to afford the title compound (32 mg). 1H NMR (400 MHz, CDCl3) δ7.42 (s, 1H), 7.34 (s, 1H), 6.83 (d, 1H), 6.60 (d, 1H), 6.39-6.36 (dd, 1H), 4.05 (s, 3H), 3.92 (s, 3H), 3.19-3.12 (m, 1H), 1.21 (d, 6H). MS (APCI−) Calc: 407.1, Found: 406.2 (M−1).

Workup

  1. customthe reaction was quenched with methanol (0.5 mL)
  2. stirringstirred for 15 minutes
  3. additiondiluted with water (10 mL)
  4. stirringstirred for another 15 minutes
  5. extractionThe solution was extracted with methylene chloride (3 times 5 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by preparative thin layer chromatography (3% methanol in methylene chloride)

Sources & evidence

ORD record
ord-e9d48344c9b641b19708063dbfec1a1e
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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