Boron tribromide → HCID 58547191, compound

HRID 1850352Notes

Reaction equation

HRID 1850352 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:14]3[CH2:17][N:16]([C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][C:3]=1[O:28]C.B(Br)(Br)Br>ClCCCl.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:14]3[CH2:17][N:16]([C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][C:3]=1[OH:28]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 54675581HCID 54675581, compound

Product 1

HCID 58547191HCID 58547191, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a solution of 2-{3-[3-(4-fluoro-3-methoxy-phenyl)-pyrazin-2-yl]-azetidin-1-yl}-quinoline (193 mg, 0.5 mmol) in 1,2-dichloro-ethane (5 mL) was added BBr3 (250 mg, 1.0 mmol). The reaction mixture was stirred at RT for 2 h. The reaction mixture was diluted with water, extracted with DCM (2×30 mL). The combined organic extracts were washed with water (20 mL) and brine (20 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel to give 2-fluoro-5-[3-(1-quinolin-2-yl-azetidin-3-yl)-pyrazin-2-yl]-phenol (111 mg, 0.31 mmol yield 62%).

Workup

  1. extractionextracted with DCM (2×30 mL)
  2. washThe combined organic extracts were washed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-e55f0277b9f84e50ba066fce9e1dc8cd
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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