Allyl bromide → HCID 67421467, compound

HRID 1987394Notes

Reaction equation

HRID 1987394 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)[CH:31]=[CH2:32]>C1COCC1>[CH2:32]([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)[CH:31]=[CH2:30]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 67421788HCID 67421788, compound

Product 1

HCID 67421467HCID 67421467, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 (202 mg, 0.56 mmol) in THF (5 mL) at 0° C. was added NaH (60%, 8 mg, 0.21 mmol). After 30 min at 0° C., allyl bromide (16 mL, 0.19 mmol) was added. After 4 h, the reaction mixture was concentrated to afford an orange solid. Purification by radial chromatography on silica gel (2 mm plate; using CH2Cl2/CH3OH/NH4OH; 50:1:1→10:1:1) afforded the product as a pale yellow oil (25 mg, 33%). 1H NMR (CDCl3) δ 1.58-1.73 (m, 3H), 1.95-2.08 (m, 3H), 2.38-2.48 (m, 8H), 2.93 (s, 2H), 4.14 (d, 2H, J=9.0 Hz), 4.27 (d, 2H, J=6.0 Hz), 5.02 (d, 1H, J=18.0 Hz), 5.16 (d, 1H, J=9.0 Hz), 5.71-5.84 (m, 1H), 5.96 (s, 1H), 7.06 (dd, 2H, J=6.0, 3.0 Hz), 7.12 (s, 1H), 7.40 (d, 2H, J=9.0 Hz), 8.46 (s, 2H). 13C NMR (CDCl3) δ 19.21, 23.68, 25.45, 30.08, 31.94, 49.56, 62.43, 114.86, 118.69, 122.07, 131.27, 133.15, 136.13, 138.79, 141.84, 147.25, 160.74. ES-MS m/z 402 [M+H]+. Anal. Calcd. for C25H31N5.1.5H2O: C, 70.06; H, 8.00; N, 16.34. Found: C, 70.19; H, 7.98; N, 16.05.

Workup

  1. waitAfter 4 h
  2. concentrationthe reaction mixture was concentrated
  3. customto afford an orange solid
  4. customPurification by radial chromatography on silica gel (2 mm plate; using CH2Cl2/CH3OH/NH4OH; 50:1:1→10:1:1)

Sources & evidence

ORD record
ord-eb6847692d964b87804f99f7589fa123
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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