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Phosphorus oxychloride → 2-(5-bromopyridine-3-yl)-1-phenyl-1H-benzimidazole

HRID 520824
Notes
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Reaction equation

HRID 520824 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O.P(Cl)(Cl)(Cl)=O>O1CCOCC1>[Br:1][C:2]1[CH:23]=[C:6]([C:7]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=2)[CH:5]=[N:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 706542275-bromo-N-(2-(phenylamino)phenyl)nicotinamide

Product 1

HCID 230940852-(5-bromopyridine-3-yl)-1-phenyl-1H-benzimidazoleYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Compound 1E (20.0 g, 54.3 mmol) was dissolved in 1,4-dioxane (anhydrous, 150 mL). Phosphorous oxychloride (36 g, 235 mmol) was then added dropwise. The resulting solution was heated at about 100° C. overnight; solids formed. After cooling to RT, the mixture was poured into hexanes (250 mL) to form additional precipitate. Solids were filtered then redissolved in DCM (200 mL) and washed with potassium carbonate (200 mL, saturated solution). The organic phase was collected, dried over sodium sulfate, and loaded onto silica gel. Short silica plug (20% ethyl acetate in hexanes and precipitation from hexanes gave 16.86 g of Compound 1F; 89% yield, pure by HNMR.

Workup

  1. customsolids formed
  2. temperatureAfter cooling to RT
  3. customto form additional precipitate
  4. filtrationSolids were filtered
  5. dissolutionthen redissolved in DCM (200 mL)
  6. washwashed with potassium carbonate (200 mL, saturated solution)
  7. customThe organic phase was collected
  8. dry with materialdried over sodium sulfate
  9. customShort silica plug (20% ethyl acetate in hexanes and precipitation from hexanes

Sources & evidence

ORD record
ord-20b39a85af3e49d2ae7fa92bd31b5f13
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09328094B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes