Benzyl Bromide → HCID 67421409, compound

HRID 1987393Notes

Reaction equation

HRID 1987393 reaction equation
[N:1]1[CH:5]=[C:4]([CH2:6][CH2:7][N:8]2[CH:13]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=3)[CH2:12][CH2:11][CH2:10][CH:9]2[C:21]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][N:22]=2)[NH:3][CH:2]=1.[H-].[Na+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[CH2:30]([N:1]1[CH:5]=[C:4]([CH2:6][CH2:7][N:8]2[CH:9]([C:21]3[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][N:22]=3)[CH2:10][CH2:11][CH2:12][CH:13]2[C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=2)[N:3]=[CH:2]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 67421788HCID 67421788, compound

Product 1

HCID 67421409HCID 67421409, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1′-[2-(3H-imidazol-4-yl)-ethyl]-3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (191 mg, 0.53 mmol) in THF (5 mL) at 0° C. was added NaH (60%, 8 mg, 0.20 mmol). After stirring at 0° C. for 30 min, benzyl bromide (21 μL, 0.18 mmol) was added and the resulting mixture was stirred overnight at room temperature. The next morning the mixture was concentrated under reduced pressure to afford a brown residue. Purification by radial chromatography on silica gel (1 mm plate; using CH2Cl2/MeOH/NH4OH; 50:1:1→10:1:1) afforded the product as a yellow oil (39 mg, 48%). 1H NMR (CDCl3) δ 1.57-1.70 (m, 3H), 1.93-2.16 (m, 5H), 2.46 (br s, 8H), 4.12 (d, 2H, J=9.0 Hz), 4.36 (s, 2H, 4.83 (s, 2H), 5.94(s, 1H), 6.99 (br s, 4H), 7.17 (s, 1H), 7.28 (s, 3H), 7.36 (d, 2H, J=9.0 Hz), 8.42 (s, 2H). 13C NMR (CDCl3) δ 19.23, 23.41, 25.39, 32.47, 50.23, 50.97, 62.04, 115.12, 122.07, 127.64, 128.49, 129.23, 136.52, 138.84, 147.33, 160.82. ES-MS m/z 452 [M+H]+. Anal. Calcd. for C29H33N5.0.5CH2Cl2: C, 71.71; H, 6.94; N, 14,17. Found: C, 71.78; H, 7.23; N, 14.10.

Workup

  1. stirringthe resulting mixture was stirred overnight at room temperature
  2. concentrationThe next morning the mixture was concentrated under reduced pressure
  3. customto afford a brown residue
  4. customPurification by radial chromatography on silica gel (1 mm plate; using CH2Cl2/MeOH/NH4OH; 50:1:1→10:1:1)

Sources & evidence

ORD record
ord-b019acebae3244c3a6e5db33dc6cbcf0
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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