Phosphorus oxybromide → HCID 86607512, compound

HRID 1465947Notes

Reaction equation

HRID 1465947 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:13]=[C:12](O)[C:11]2[C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[CH:16][S:17][C:10]=2[C:9]=1[OH:25])=[O:7])[CH2:2][CH2:3][CH3:4].P(Br)(Br)([Br:28])=O>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[CH2:1]([O:5][C:6]([C:8]1[N:13]=[C:12]([Br:28])[C:11]2[C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[CH:16][S:17][C:10]=2[C:9]=1[OH:25])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178450839HCID 178450839, compound

Product 1

HCID 86607512HCID 86607512, compoundYield 55.9%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

3-(4-Fluoro-phenyl)-4,7-dihydroxy-thieno[3,2-c]pyridine-6-carboxylic acid butyl ester (77.9 mg, 0.216 mmol), example 30-f, was suspended in 1.1 mL of anhydrous toluene. Phosphorous oxybromide (0.155 g, 0.539 mmol) was added, and the reaction mixture was heated at 120° C. for 20 min. using a CEM microwave reactor (CEM, Matthews, N.C.). The reaction mixture was diluted with ethyl acetate, and saturated sodium bicarbonate solution was then added. The biphasic mixture was stirred for 15 min. and separated to isolate the organic fraction. The organic fraction was washed with brine, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by column chromatography eluting from silica gel with dichloromethane to produce 51.2 mg of the title compound. MS: (−) m/z 422.1, 424.1 (M−1, 79Br/81Br).

Workup

  1. additionwas then added
  2. customseparated
  3. customto isolate the organic fraction
  4. washThe organic fraction was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography
  8. washeluting from silica gel with dichloromethane

Sources & evidence

ORD record
ord-2db67f3e60e5470b80009482f0088860
Source dataset
uspto-grants-2015_04
Patent number
US09000006B2

Reaction notes

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