Bromide ion → HCID 57666057, compound

HRID 889695Notes

Reaction equation

HRID 889695 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH:5]([C:10]1[CH:11]=[C:12]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH:18]([C:22]([F:25])([F:24])[F:23])[NH:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].[CH3:37][O:38][C:39]1[CH:46]=[CH:45][C:42]([CH2:43]Br)=[CH:41][CH:40]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br-]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CCN(C(C)C)C(C)C>[CH2:1]([O:3][C:4](=[O:36])[CH:5]([C:10]1[CH:11]=[C:12]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:31]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH:18]([C:22]([F:23])([F:24])[F:25])[N:17]2[CH2:43][C:42]2[CH:45]=[CH:46][C:39]([O:38][CH3:37])=[CH:40][CH:41]=2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

7

Reactant 4

HCID 259Bromide ionHCID 10796Cesium carbonate2×HCID 1650214-Methoxybenzyl bromideHCID 57665930HCID 57665930, compound

Product 1

HCID 57666057HCID 57666057, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalyst2×HCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
80 °C

Procedure

4-Methyl-2-[4′-trifluoromethyl-5-(6-trifluoromethyl-piperidin-2-yl)-biphenyl-3-yl]-pentanoic acid ethyl ester, compound 7b (47 mg, 0.092 mmol), 4-Methoxybenzyl bromide (66 μl, 0.46 mmol), DIEA (160 μl, 0.919), and tetrabutylammonium iodide (TBAI)(36 mg, 0.096 mmol) were combined and heated to 80° C. After overnight, no product was formed. Cesium carbonate (30 mg, 0.46 mmol) was added and after 5.5 hours ˜30% product was obtained. Additional Cesium carbonate (30 mg), bromide (66 ml) and TBAI were added and the reaction continued 72 hours. Little change in product formation. Reaction was purified directly by silica gel chromatography to give 21.3 mg, 36% as a clear oil. (M+H) 635.38, Found 636.4.

Workup

  1. customno product was formed
  2. customwas obtained
  3. waitthe reaction continued 72 hours
  4. customReaction
  5. customwas purified directly by silica gel chromatography
  6. customto give 21.3 mg, 36% as a clear oil

Sources & evidence

ORD record
ord-37f4508297384c478bc39036733246d4
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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