Benzyl Bromide → HCID 22327345, compound

HRID 1866474Notes

Reaction equation

HRID 1866474 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[NH:13][C:14]4[C:19]([C:20]=3[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:18][CH:17]=[CH:16][CH:15]=4)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:26][CH2:27][C:28]#[N:29].CC([O-])(C)C.[K+].[CH:36]1[CH:41]=[CH:40][C:39]([CH2:42]Br)=[CH:38][CH:37]=1>C1COCC1>[CH2:42]([N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:12]1[C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([Br:1])=[C:3]([O:26][CH2:27][C:28]#[N:29])[CH:4]=[CH:5]2)[C:39]1[CH:40]=[CH:41][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 22327341HCID 22327341, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22327345HCID 22327345, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of {[1-bromo-6-(3-pentyl-1H-indol-2-yl)-2-naphthyl]oxy}acetonitrile (0.135 g, 0.257 mmol) in THF (5 mL) at 0° C. was added KOt-Bu (0.032 g, 0.283 mmol) followed by BnBr (0.019 mL, 0.308 mmol). The reaction was warmed to rt and let stir for 24 h. After this time, the reaction mixture was quenched with 1 N HCl (˜2 mL). The resulting solution was diluted with EtOAc (100 mL). The organic layer was washed with 1 N HCl (10 mL), sat. aq. NaHCO3 (10 mL), and brine (10 mL) and then dried (MgSO4). After concentration, the residue was purified by preparatory plate chromatography (20% EtOAc:petroleum ether) to afford the product (0.105 g, 56%) as a solid; 1H NMR (DMSO-d6) δ 0.73 (t, J=7.4 Hz, 3H), 1.09-1.23 (m, 4H), 1.47-1.63 (m, 2H), 2.70 (t, J=7.7 Hz, 2H), 5.34 (s, 2H), 5.46 (s, 2H), 6.81 (d, J=7.4 Hz, 2H), 7.04-7.23 (m, 5H), 7.41 (d, J=8.1 Hz, 1H), 7.62-7.73 (m, 3H), 8.02 (s, 1H), 8.12 (d, J=9.2 Hz, 1H), 8.20 (d, J=9.2 Hz, 1H); mass spectrum [(+) ESI], m/z 537/539 (M+H)+.

Workup

  1. customAfter this time, the reaction mixture was quenched with 1 N HCl (˜2 mL)
  2. additionThe resulting solution was diluted with EtOAc (100 mL)
  3. washThe organic layer was washed with 1 N HCl (10 mL), sat. aq. NaHCO3 (10 mL), and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationAfter concentration
  6. customthe residue was purified by preparatory plate chromatography (20% EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-181e2339ae1e4980be0529f7b8247545
Source dataset
uspto-grants-2009_12
Patent number
US07629377B2

Reaction notes

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