2-Pyridyl isothiocyanate → HCID 89783777, compound

HRID 1056283Notes

Reaction equation

HRID 1056283 reaction equation
[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[N:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)=[C:13]=[S:14]>CCO>[Br:11][C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:2]=1[NH:1][C:13](=[S:14])[N:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:4]2=[O:6]

Participants

4

Reactant 2

HCID 992362-Pyridyl isothiocyanateHCID 2702592-Amino-3-bromobenzoic acid

Product 1

HCID 89783777HCID 89783777, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-3-bromobenzoic acid (705 mg, 3.26 mmol, Sigma Aldrich) and 2-isothiocyanatopyridine (800 mg, 5.87 mmol, 415a) in EtOH (19.6 mL) was set stirring at RT, and TEA (0.68 mL, 4.90 mmol) was added dropwise. It was sealed and heated to 100° C. for 16 h. The mixture was concentrated under reduced pressure to a residue that was taken up in DCM. Silica was added, and the crude reaction was adsorbed. It was purified on 24 g SiO2 (eluent: 0-100% EtOAc/hexanes over 30 min, RediSep Gold). The product fractions were combined and concentrated under reduced pressure to give a yellow-orange solid (311 mg, 29%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.18 (1H, br. s.) 8.60 (1H, d, J=4.69 Hz) 8.39 (1H, d, J=4.11 Hz) 8.11 (1H, d, J=6.85 Hz) 7.83-7.93 (1H, m) 7.78 (1H, dd, J=7.82, 1.37 Hz) 7.44-7.53 (2H, m). m/z (ESI, +ve) 333.8 (M+H)+.

Workup

  1. customIt was sealed
  2. temperatureheated to 100° C. for 16 h
  3. concentrationThe mixture was concentrated under reduced pressure to a residue that
  4. additionSilica was added
  5. customthe crude reaction
  6. customIt was purified on 24 g SiO2 (eluent: 0-100% EtOAc/hexanes over 30 min, RediSep Gold)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ad088757936e40969b251c921f5bfcd8
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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