N-Allyl-2,2,2-trifluoroacetamide → (E)-N-(3-(3-(cyclohexylmethoxy)-5-fluorophenyl)allyl)-2,2,2-trifluoroacetamide

HRID 74425Notes

Reaction equation

HRID 74425 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([O:9][CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:3]=1.[CH2:17]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH:18]=[CH2:19]>CN(C=O)C>[CH:11]1([CH2:10][O:9][C:4]2[CH:3]=[C:2](/[CH:19]=[CH:18]/[CH2:17][NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH:7]=[C:6]([F:8])[CH:5]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 558569N-Allyl-2,2,2-trifluoroacetamideHCID 673171711-Bromo-3-(cyclohexylmethoxy)-5-fluorobenzene

Product 1

HCID 86637624(E)-N-(3-(3-(cyclohexylmethoxy)-5-fluorophenyl)allyl)-2,2,2-trifluoroacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Coupling of 1-bromo-3-(cyclohexylmethoxy)-5-fluorobenzene with N-allyl-2,2,2-trifluoroacetamide following the method used in Example 10 except DMF was used as solvent gave (E)-N-(3-(3-(cyclohexylmethoxy)-5-fluorophenyl)allyl)-2,2,2-trifluoroacetamide as a white solid. Yield (0.44 g, 64%): 1H NMR (400 MHz, DMSO-d6) 1H NMR (400 MHz, CDCl3) δ 9.68 (t, J=4.0 Hz, 1H), 6.79-6.86 (m, 2H), 6.65 (dt, J=10.8, 2.0 Hz, 1H), 6.45 (d, J=15.6 Hz, 1H), 6.31 (dt, J=16.0, 5.6 Hz, 1H), 3.95 (t, J=4.8 Hz, 2H), 3.77 (d, J=5.6 Hz, 2H), 1.58-1.80 (m, 6H), 1.10-1.28 (m, 3H), 0.90-1.06 (m, 2H).

Sources & evidence

ORD record
ord-47b2bc42018d4f9490d67901854a4184
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

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