Boron tribromide → 2-(6-Hydroxy-2-naphthyl)-3-pentyl-1H-indole

HRID 1866472Notes

Reaction equation

HRID 1866472 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[NH:14][C:15]3[C:20]([C:21]=1[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:7]=[CH:6]2.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[NH:14][C:15]3[C:20]([C:21]=1[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 223273422-(6-methoxy-2-naphthyl)-3-pentyl-1H-indole

Product 1

HCID 223273352-(6-Hydroxy-2-naphthyl)-3-pentyl-1H-indoleYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(6-methoxy-2-naphthyl)-3-pentyl-1H-indole (0.915 g, 2.66 mmol) in CH2Cl2 (30 mL) cooled to −78° C. was added BBr3 (9.86 mL, 1.0 M in CH2Cl2, 9.86 mmol) dropwise. The reaction was stirred at this temperature for 0.5 h and then warmed to rt for 2 h. The reaction mixture was quenched with MeOH (−5 mL) followed by dilution with H2O (20 mL) and EtOAc (200 mL). The organic layer was washed with brine (20 mL) and then dried (Na2SO4). After concentration, the residue was purified by the Biotage Flash 40 apparatus (10 to 20% EtOAc:petroleum ether gradient) to afford the product (0.677 g, 77%) as a foamy solid; 1H NMR (DMSO-d6) δ 0.83 (t, J=7.3 Hz, 3H), 1.23-1.42 (m, 4H), 1.58-1.76 (m, 2H), 2.89 (t, J=8.2 Hz, 2H), 7.00 (t, J=8.2 Hz, 1H), 7.06-7.19 (m, 3H), 7.35 (d, J=8.2 Hz, 1H), 7.53 (d, J=8.2, 1H), 7.67 (d, J=9.1 Hz, 1H), 7.74-7.88 (m, 2H), 7.98 (s, 1H), 9.83 (s, 1H), 11.14 (s, 1H); mass spectrum [(+) ESI], m/z 330 (M+H)+ and [(−) ESI], m/z 328 (M−H)−.

Workup

  1. customThe reaction mixture was quenched with MeOH (−5 mL)
  2. washThe organic layer was washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationAfter concentration
  5. customthe residue was purified by the Biotage Flash 40 apparatus (10 to 20% EtOAc:petroleum ether gradient)

Sources & evidence

ORD record
ord-6852601ea6314b60ba015c35f49ccd03
Source dataset
uspto-grants-2009_12
Patent number
US07629377B2

Reaction notes

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