Tetrahydrofuran → HCID 86634783, compound

HRID 911072Notes

Reaction equation

HRID 911072 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]([Br:14])=[CH:4][N:3]=1.C1COCC1.[C:20]([N:28]=[C:29]=[S:30])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)(=O)C.CCCCCC>[C:20]([NH:28][C:29](=[S:30])[NH:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]([Br:14])=[CH:4][N:3]=1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 68284Benzoyl isothiocyanateHCID 66617942HCID 66617942, compound

Product 1

HCID 86634783HCID 86634783, compoundYield 85.22%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A flask was charged with ethyl 2-(2-amino-5-bromopyridin-4-yl)acetate (2.700 g, 10.42 mmol) and THF (20 mL), and benzoyl isothiocyanate (1.546 mL, 11.46 mmol) was added. The mixture was stirred overnight at ambient temperature. The thick slurry was diluted with 50 mL of 10% ethyl acetate/hexane and filtered. The filter cake was washed with 10% ethyl acetate/hexane and dried to afford the desired product (3.75 g, 85.22%) as a pale yellow fluffy solid.

Workup

  1. additionwas added
  2. filtrationfiltered
  3. washThe filter cake was washed with 10% ethyl acetate/hexane
  4. customdried

Sources & evidence

ORD record
ord-33b3850bc0bf4d96bdd7242b6f94e32b
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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