Stannous chloride dihydrate → HCID 86677533, compound

HRID 1497904Notes

Reaction equation

HRID 1497904 reaction equation
[F:1][C:2]1([F:21])[CH2:4][CH:3]1[C:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[C:14]([N+:16]([O-])=O)[C:13]([CH3:19])=[CH:12][C:11]=2[CH3:20])[N:6]=1.O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(O)C>[F:21][C:2]1([F:1])[CH2:4][CH:3]1[C:5]1[O:9][N:8]=[C:7]([C:10]2[C:11]([CH3:20])=[CH:12][C:13]([CH3:19])=[C:14]([CH:15]=2)[NH2:16])[N:6]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 71280814HCID 71280814, compound

Product 1

HCID 86677533HCID 86677533, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

A stirring mixture of 5-(2,2-difluorocyclopropyl)-3-(2,4-dimethyl-5-nitrophenyl)-1,2,4-oxadiazole (149) (190 mg, 0.644 mmol) and tin (II) chloride dihydrate (581 mg, 2.57 mmol) in ethanol (10 mL) was heated at 78° C. for 2 hours. The reaction was cooled to room temperature and the pH was adjusted to basic with a saturated solution of sodium bicarbonate. The resulting solid was filtered through a plug of celite and washed with excess ethanol. The solvent was partially reduced and the crude product was extracted with ethyl acetate. The organic was washed with water, brine and dried over anhydrous sodium sulfate. The solvent was concentrated and the crude product was purified by silica chromatography. 1H NMR (400 MHz, d6-DMSO) δ 7.21 (s, 1H), 6.93 (s, 1H), 4.96 (s, 2H), 3.70-3.62 (m, 1H), 2.47-2.41 (m, 1H), 2.37-2.28 (m, 1H), 2.35 (s, 3H), 2.08 (s, 3H). MS m/z 266.10 (M+1)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationThe resulting solid was filtered through a plug of celite
  3. washwashed with excess ethanol
  4. extractionthe crude product was extracted with ethyl acetate
  5. washThe organic was washed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe solvent was concentrated
  8. customthe crude product was purified by silica chromatography

Sources & evidence

ORD record
ord-8508e844297f4d39a77746b0c41c7b8e
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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