2-Bromo-4'-methylacetophenone → Fatostatin A

HRID 1503348Notes

Reaction equation

HRID 1503348 reaction equation
[CH3:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]([NH2:12])=[S:11])[CH:7]=[CH:8][N:9]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)=O>C(O)C>[CH3:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]2[S:11][CH:14]=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=3)[N:12]=2)[CH:7]=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 692722-Bromo-4'-methylacetophenoneHCID 666418Prothionamide

Product 1

HCID 1889993Fatostatin AYield 106.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of prothionamide (1.03 g, 5.70 mmol) and 2-bromo-4′-methylacetophenone (1.22 g, 5.70 mmol) in ethanol (20 ml) was heated at 70° C. with stirring for 0.5 h, and then cooled to 0° C. A yellow precipitate formed was filtered, washed with cold ethanol, and dried to give 2-propyl-4-(4-p-tolylthiazol-2-yl)pyridine (fatostatin) 1 HBr salt (1.78 g, 83%) as yellow needles. mp: 190-193° C.; 1H NMR (600 MHz, DMSO-d6): δ 8.88 (d, J=6.2 Hz, 1H), 8.54 (s, 1H), 8.46 (d, J=1.4 Hz, 1H), 8.36 (dd, J=1.4, 6.2 Hz, 1H), 7.99 (d, J=7.6 Hz, 2H), 7.31 (d, J=7.6 Hz, 2H), 3.03 (t, J=7.6 Hz, 2H), 2.35 (s, 3H), 1.80 (m, 2H), 0.96 (t, J=7.6 Hz, 3H); 13C NMR (150 MHz, DMSO-d6): δ 161.3, 158.5, 156.9, 146.2, 143.2, 138.4, 130.4, 129.5, 126.3, 122.3, 120.3, 119.5, 35.0, 22.4, 20.9, 13.4; HRMS (m/z): [M+H]+ calcd for C18H19N2S, 295.1269; found, 295.1269.

Workup

  1. temperaturecooled to 0° C
  2. customA yellow precipitate formed
  3. filtrationwas filtered
  4. washwashed with cold ethanol
  5. customdried

Sources & evidence

ORD record
ord-82c6d673595944e38bd25fc7b37b0e1d
Source dataset
uspto-grants-2015_12
Patent number
US09212179B2

Reaction notes

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