3-Bromo-2-methyl-1-propene → HCID 59161724, compound

HRID 2427867Notes

Reaction equation

HRID 2427867 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[N:8]=[C:7]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:6]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br[CH2:43][C:44]([CH3:46])=[CH2:45]>C1COCC1>[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:5]1[CH:6]=[C:7]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:23][CH:22]=2)[N:8]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=2)[CH:10]=1)[CH2:45][C:44]([CH3:46])=[CH2:43]

Participants

5

Reactant 3

HCID 3577853-Bromo-2-methyl-1-propeneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 59161726HCID 59161726, compound

Product 1

HCID 59161724HCID 59161724, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [2,6-bis-(4-trifluoromethylphenyl)-pyridin-4-yl]-acetic acid methyl ester (1.18 g, 2.69 mmol) in THF (30 mL) at −78° C. under argon was added potassium bis(trimethylsilyl)amide (0.5 M solution in toluene, 5.38 mL, 2.69 mmol). After stirring for 30 minutes, 3-bromo-2-methylpropene (273 μL, 2.69 mmol) was added and stirred for an additional 30 minutes. The reaction mixture was allowed to warm up slowly and stirred for another 30 minutes at 0° C. The mixture was then concentrated and purified by column chromatography on silica gel (0-8% ethyl acetate in heptane) to give the product as a white solid (940 mg, 71%). 1H NMR (300 MHz, CDCl3) δ 8.24 (d, J=8.29 Hz, 4H), 7.76 (d, J=8.29 Hz, 4H), 7.74 (s, 2H), 4.79 (d, J=19.59 Hz, 2H), 3.97 (dd, J=6.78, 9.04 Hz, 1H), 3.72 (s, 3H), 2.95 (dd, J=8.85, 14.51 Hz, 1H), 2.56 (dd, J=6.59, 14.51 Hz, 1H), 1.78 (s, 3H). MS m/e 494.2 (M+H)

Workup

  1. stirringstirred for an additional 30 minutes
  2. temperatureto warm up slowly
  3. stirringstirred for another 30 minutes at 0° C
  4. concentrationThe mixture was then concentrated
  5. custompurified by column chromatography on silica gel (0-8% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-b991ac5f3d394d208abdb1578f1f38be
Source dataset
uspto-grants-2011_06
Patent number
US07968725B2

Reaction notes

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