1-Bromohexane → HCID 11540943, compound

HRID 551929Notes

Reaction equation

HRID 551929 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][NH:18][C:19]3[CH:31]=[CH:30][C:22]4[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[O:26][C:21]=4[CH:20]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].Br[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>CS(C)=O.CCOC(C)=O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][N:18]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:19]3[CH:31]=[CH:30][C:22]4[C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:28])[O:26][C:21]=4[CH:20]=3)=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 114192887-[4-(4-Butyl-phenylethynyl)-benzylamino]-2,2-dimethyl-benzo[1,3]dioxin-4-one

Product 1

HCID 11540943HCID 11540943, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-[4-(4-butyl-phenylethynyl)-benzylamino]-2,2-dimethyl-benzo[1,3]-dioxin-4-one (1.16 g, 2.64 mmol) in DMSO (32 mL) was added sodium hydride (159 mg, 3.96 mmol, 55-65% in oil) and the resulting mixture was stirred 2 min at rt, then 1-bromohexane (559 μl, 3.96 mmol) was added. The red solution was stirred at rt for 2 hrs. The reaction mixture was poured in EtOAc (70 mL) and washed with an aqueous solution of HCl (2×30 mL, 0.1N) and water (6×30 mL). The organic layer was dried over MgSO4 and the solvents were removed under reduced pressure. The crude mixture was purified by flash chromatography on silicagel (c-Hex/EtOAc (6/1)) to give 795 mg (56%) of the title compound as a yellow oil. HPLC, Rt: 6.4 min (purity: 98.3%). M+(ESI): 524.5. 1H NMR (CDCl3) δ: 7.71 (d, J=8.7 Hz, 1H), 7.47 (d, J=8.3 Hz, 2H), 7.41 (d, J=7.9 Hz, 2H), 7.13 (m, 4H), 6.36 (m, 1H), 6.04 (m, 1H), 4.58 (s, 2H), 3.40 (t, J=7.7 Hz, 2H), 2.61 (t, J=7.7 Hz, 2H), 1.76-1.48 (m, 8H), 1.42-1.20 (m, 10H), 0.95-0.82 (m, 6H).

Workup

  1. stirringThe red solution was stirred at rt for 2 hrs
  2. washwashed with an aqueous solution of HCl (2×30 mL, 0.1N) and water (6×30 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvents were removed under reduced pressure
  5. customThe crude mixture was purified by flash chromatography on silicagel (c-Hex/EtOAc (6/1))

Sources & evidence

ORD record
ord-5cdc0e3ccfd540bdad971ccc2a693e52
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

Loading…