Boron tribromide → HCID 57845448, compound

HRID 734398Notes

Reaction equation

HRID 734398 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13]C)[CH:11]=2)[C:6]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:5]1)(=[O:3])[CH3:2].B(Br)(Br)Br>ClCCl>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[C:6]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57845369HCID 57845369, compound

Product 1

HCID 57845448HCID 57845448, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl (1-acetyl-6-methoxy-1H-indol-3-yl)acetate (0.67 g, 2.56 mmol) (Example 13) in dichloromethane (10 mL) was added 1 M BBr3 in dichloromethane (10.3 mL, 10.3 mmol) at −78° C. under argon. Stirring was continued at −78° C. for 1 h, at 0° C. for 3 h and at rt for 18 h consecutively. The reaction mixture was quenched with water and dichloromethane was added. Solid NaHCO3 was added to adjust the pH of the mixture to 8. The mixture was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to yield a yellow solid (200.0 mg, 32%). LC/MS m/z 248 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ 9.42 (s, 1H), 7.77 (d, 1H), 7.52 (s, 1H), 7.28 (d, 1H), 6.71 (dd, 1H), 3.71 (s, 2H), 3.61 (s, 3H), 2.55 (s, 3H).

Workup

  1. customThe reaction mixture was quenched with water and dichloromethane
  2. additionwas added
  3. additionSolid NaHCO3 was added
  4. extractionThe mixture was extracted with CH2Cl2
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c84d2f8e4bfd473da0d0e21644d9d50a
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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