Phosphorus oxybromide → HCID 136343979, compound

HRID 1847258Notes

Reaction equation

HRID 1847258 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[C:9]([OH:19])=[C:10]2[C:17]([CH3:18])=[N:16][S:15][C:11]2=[C:12](O)[N:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4].C(OC(C1N=C(O)C2C(C)=NSC=2C=1O)=O)CCC.P(Br)(Br)([Br:41])=O>ClC(Cl)C>[CH2:1]([O:5][C:6]([C:8]1[C:9]([OH:19])=[C:10]2[C:17]([CH3:18])=[N:16][S:15][C:11]2=[C:12]([Br:41])[N:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 178450853HCID 178450853, compoundHCID 178450867HCID 178450867, compound

Product 1

HCID 136343979HCID 136343979, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of the mixture of 4,7-dihydroxy-3-methyl-isothiazolo[5,4-c]pyridine-5-carboxylic acid butyl ester and 4,7-dihydroxy-3-methyl-isothiazolo[4,5-c]pyridine-6-carboxylic acid butyl ester (6.67 mmol) obtained as described above in dichloroethane (33.3 mL) was added POBr3 (8.0 mmol). The reaction mixture was stirred at 120° C. in a microwave oven for 35 min. After cooling to r.t., the mixture was partitioned between CH2Cl2 and sat. NaHCO3, then filtered and the organic layer of the filtrate was washed with brine before it was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel. Eluting with 0-20% EtOAc/CH2Cl2, gave 7-bromo-4-hydroxy-3-methyl-isothiazolo[5,4-c]pyridine-5-carboxylic acid butyl ester (850 mg) as a white solid: MS (m/z) 342.9 (M−1), 345.0 (M−1), and 4-Bromo-7-hydroxy-3-methyl-isothiazolo[4,5-c]pyridine-6-carboxylic acid butyl ester (473 mg) as a white solid: MS (m/z) 342.9 (M−1), 345.0 (M−1).

Workup

  1. customobtained
  2. temperatureAfter cooling to r.t.
  3. customthe mixture was partitioned between CH2Cl2 and sat. NaHCO3
  4. filtrationfiltered
  5. washthe organic layer of the filtrate was washed with brine before it
  6. dry with materialwas dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washEluting with 0-20% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-f2878f07c9db48dbb210467ca20a10f7
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

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