Sodium Hydroxide → HCID 11687354, compound

HRID 270620Notes

Reaction equation

HRID 270620 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10](O)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:13])[CH:8]=2)[N:3]=1.P(Br)(Br)([Br:16])=O.[OH-].[Na+]>P(Br)(Br)Br>[NH2:1][C:2]1[CH:11]=[C:10]([Br:16])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:13])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24613Phosphorus oxybromideHCID 178507936HCID 178507936, compound

Product 1

HCID 11687354HCID 11687354, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 24614Phosphorus tribromideSolvent

Procedure

1 (7.2 g) was heated with POBr3 (22.0 g) in PBr3 (20 ml) at 140-160° C. under N2 for 19 hours. The reaction was cooled, carefully basified with 2 M NaOH (250 mL) and thrice extracted with CHCl3 (30 mL). The organic layer was concentrated, and the residue purified by silica gel chromatography using CHCl3/acetone/Et3N (75:25:1) to afford the product that was re-crystallized from benzene/CH2Cl2/hexane to furnish off-white crystals (5.5 g, 57% yield): 1H NMR (CDCl3) δ 4.70 (bs, 2 H, NH2), 7.10 (s, 1 H), 7.37 (m, 1 H), 7.66 (m, 2 H); HRMS-FAB (M+) calculated for 239.9698, found 239.9707.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with CHCl3 (30 mL)
  3. concentrationThe organic layer was concentrated
  4. customthe residue purified by silica gel chromatography
  5. customto afford the product that
  6. customwas re-crystallized from benzene/CH2Cl2/hexane

Sources & evidence

ORD record
ord-2f3118b1f8f7473598d9daca62608cd0
Source dataset
uspto-grants-2008_11
Patent number
US07449571B2

Reaction notes

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