Tetrahydrofuran → (6-Chloro-4-methyl-pyridin-2-yl)-(2-methyl-allyl)-(4-trifluoromethyl-phenyl)-amine

HRID 2427882Notes

Reaction equation

HRID 2427882 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[CH:5]=[C:4]([CH3:19])[CH:3]=1.[H-].[Na+].BrC=[CH:24][CH2:25][CH3:26].[CH2:27]1COCC1>>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:27][C:25]([CH3:24])=[CH2:26])[C:9]2[CH:10]=[CH:11][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:14]=2)[CH:5]=[C:4]([CH3:19])[CH:3]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 359451-Bromobut-1-eneHCID 59161720(6-Chloro-4-methyl-pyridin-2-yl)-(4-trifluoromethyl-phenyl)-amine

Product 1

HCID 59161725(6-Chloro-4-methyl-pyridin-2-yl)-(2-methyl-allyl)-(4-trifluoromethyl-phenyl)-amineYield 68%

Procedure

To a solution of (6-chloro-4-methyl-pyridin-2-yl)-(4-trifluoromethyl-phenyl)-amine (290 mg, 1.0 mmol) in THF (10 mL) was added NaH (60%, 80 mg, 2.0 mmol) and 1-bromo-3-methylpropene (150 mg, 1.1 mmol). The mixture was microwaved 20 minutes at 120° C. and concentrated. The residue was purified by chromatography on silica gel (10-30% CH2Cl2 in heptane) to give the product as a colorless oil (230 mg, 68%). 1H NMR (300 MHz, CDCl3) δ 7.58 (d, J=8.29 Hz, 2H), 7.34 (d, J=8.67 Hz, 2H), 6.59 (s, 1H), 6.45 (s, 1H), 4.81 (d, J=15.07 Hz, 2H), 4.55 (s, 2H), 2.18 (s, 3H), 1.76 (s, 3H). MS m/e 341.1 (M+H),

Workup

  1. customThe mixture was microwaved 20 minutes at 120° C.
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on silica gel (10-30% CH2Cl2 in heptane)

Sources & evidence

ORD record
ord-17be6422fbbf423d87822851b4ba6733
Source dataset
uspto-grants-2011_06
Patent number
US07968725B2

Reaction notes

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