Cyanogen Bromide → HCID 86717782, compound

HRID 1468826Notes

Reaction equation

HRID 1468826 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][O:14][CH2:15][C@@H:16]2[CH2:18][C@@H:17]2[CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:11][CH:10]=1.[CH:27]([N:30](CC)C(C)C)(C)C.N#CBr>C(#N)C>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][O:14][CH2:15][C@@H:16]2[CH2:18][C@@H:17]2[CH:19]2[CH2:24][CH2:23][N:22]([C:27]#[N:30])[CH2:21][CH2:20]2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 81531DiisopropylethylamineHCID 86717783HCID 86717783, compound

Product 1

HCID 86717782HCID 86717782, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product from step B (1.00 g, 3.08 mmol) and N,N-diisopropylethylamine (1.61 mL, 9.25 mmol) were dissolved in acetonitrile (20 mL). Cyanogen bromide (5M in acetonitrile, 0.746 mL, 3.7 mmol) was added and the reaction was stirred overnight at room temperature. The reaction was concentrated and the residue was partitioned between CH2Cl2 and water. The organic layer was saved and the aqueous layer was extracted with CH2Cl2. The organic layers were combined, washed with brine, dried over anhydrous MgSO4, filtered and evaporated to yield a crude material, which was purified by silica gel column chromatography (gradient elution 0% to 100% EtOAc in hexanes) to yield the title compound as a viscous oil.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was partitioned between CH2Cl2 and water
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washwashed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a crude material, which
  9. customwas purified by silica gel column chromatography (gradient elution 0% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-fc05dfe3715542179da1037e2a03b9be
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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