Hexafluoropropylene → HCID 86633389, compound

HRID 1470824Notes

Reaction equation

HRID 1470824 reaction equation
FF.[CH3:3][O:4][C@@H:5]1[C@H:10]([O:11][CH3:12])[C@@H:9]([O:13][CH3:14])[C@H:8]([CH3:15])[O:7][C@H:6]1[O:16][N:17]=[CH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:29]=[CH:28][N:27]([C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][N:31]=3)[N:26]=2)=[CH:21][CH:20]=1.[F:37][C:38]([F:45])([F:44])[C:39]([F:43])=[C:40]([F:42])[F:41].C(N(CC)CC)C>CN(C=O)C.C1COCC1>[CH3:3][O:4][C@@H:5]1[C@H:10]([O:11][CH3:12])[C@@H:9]([O:13][CH3:14])[C@H:8]([CH3:15])[O:7][C@H:6]1[O:16][N:17]=[CH:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[N:29]=[CH:28][N:27]([C:30]3[CH:35]=[CH:34][C:33]([O:36][C:40]([F:42])([F:41])[CH:39]([F:43])[C:38]([F:45])([F:44])[F:37])=[CH:32][N:31]=3)[N:26]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 8302HexafluoropropyleneHCID 8471TriethylamineHCID 24524FluorineHCID 86633390HCID 86633390, compound

Product 1

HCID 86633389HCID 86633389, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

Fluoroalkylation conditions were based on a paper by Timperley et al. J. Fluorine Chem. 2006, 127, 249. A solution of 4-[1-(5-hydroxy-pyridin-2-yl)-1H-[1,2,4]-triazol-3-yl]-benzaldehyde O-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl)-oxime in 10 mL anhydrous DMF/THF (1:1) under a N2 atmosphere was cooled at 0° C. while an excess of hexafluoropropylene gas was added over 15 min. Following addition, triethylamine (15 uL, 0.109 mmol) was added and the reaction mixture warmed to ambient temperature before concentration to dryness. Chromatography (EtOAc/hexanes, 1:1) afforded Compound 94 (16 mg, 24%). 1H NMR (CDCl3) δ 9.17 (s, 1H), 8.39 (d, J=7.68 Hz, 1H), 8.21 (d, J=8.22 Hz, 2H), 8.19 (s, 1H), 8.08 (d, J=7.68 Hz, 1H), 7.74 (d, J=8.22 Hz, 2H), 6.97 (s, 1H), 5.63 (d, J=1.85 Hz, 1H), 5.17 (m, 1H), 3.78 (dd, J=3.28, 1.99 Hz, 1H), 3.63 (m, 1H), 3.59 (s, 3H), 3.57 (s, 3H), 3.56 (s, 3H), 3.43 (dd, J=9.31, 3.36 Hz, 1H), 3.18 (t, J=9.48 Hz, 1H), 1.29 (d, J=6.26 Hz, 3H); EIMS 619 m/z (M+).

Workup

  1. additionwas added over 15 min
  2. additionwas added

Sources & evidence

ORD record
ord-e4d67499259140f490c4d08428b4fc1a
Source dataset
uspto-grants-2015_04
Patent number
US09006468B2

Reaction notes

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