Boron trifluoride etherate → methyl 2-(5-bromo-2-(tert-butylcarbamoyl)-1H-indol-3-yl)acetate

HRID 1819686Notes

Reaction equation

HRID 1819686 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]([O:14][CH3:15])=[O:13].[C:16]([N:20]=[C:21]=[O:22])([CH3:19])([CH3:18])[CH3:17].B(F)(F)F.CCOCC.CCOC(C)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:21](=[O:22])[NH:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[C:5]2[CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 8857Ethyl AcetateHCID 62412tert-Butyl isocyanateHCID 49782545methyl 2-(5-bromo-1H-indol-3-yl)acetate

Product 1

HCID 69057413methyl 2-(5-bromo-2-(tert-butylcarbamoyl)-1H-indol-3-yl)acetateYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step I (I): To a solution of methyl 2-(5-bromo-1H-indol-3-yl)acetate ( 268 mg, 1.0 mmol) and tert-butyl isocyanate (149 mg, 1.5 mmol) in dichloromethane was added boron trifluoride diethyl etherate dropwise at −5° C. under nitrogen. The mixture was stirred from −5° C. to rt and at rt overnight. 100 mL of EtOAc was added, and the resulting solution was washed with 0.1 N HCl and water. The organic layer was dried over Na2SO4, and the solvents was removed to give 340 mg of the crude methyl 2-(5-bromo-2-(tert-butylcarbamoyl)-1H-indol-3-yl)acetate (yield 92.6%). MS (ESI) (M+H)+=369.05. 1H NMR (500 MHz, CDCl3) δ ppm 1.51 (s, 9 H) 3.74 (s, 3 H) 3.86 (s, 2 H) 7.26 (d, J=8.55 Hz, 1 H) 7.35 (dd, J=8.55, 1.83 Hz, 1 H) 7.79 (d, J=1.53 Hz, 1 H) 8.01 (s, 1 H) 9.17 (s, 1 H).

Workup

  1. washthe resulting solution was washed with 0.1 N HCl and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvents was removed

Sources & evidence

ORD record
ord-313f12f0927c43c89f146472dccb1857
Source dataset
uspto-grants-2009_10
Patent number
US07601751B2

Reaction notes

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