Toluene → HCID 57786272, compound

HRID 1628996Notes

Reaction equation

HRID 1628996 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[C:10]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C:19]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[Cl:28])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.CC(C)([O-])C.[K+]>C(#N)C.C(OCC)(=O)C.O1CCCC1>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[C:19]1[C:6]2=[N:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:9]=3[N:5]2[CH2:4][CH2:3][CH:2]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 23665647Potassium tert-butoxideHCID 68775340HCID 68775340, compound

Product 1

HCID 57786272HCID 57786272, compoundYield 23%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [1-(3-bromopropyl)-7-(diethylamino)-1H-benzimidazol-2-yl](2,4-dichlorophenyl)methanone (Reference example 211, 360 mg, 0.745 mmol) and triphenylphosphine (586 mg, 2.23 mmol) in acetonitrile (5 mL) was stirred for 60 h at 80° C. The reaction mixture was concentrated in vacuo. Toluene (5 mL), tetrahydrofuran (1 mL), and potassium tert-butoxide (85%, 83.6 mg, 0.745 mmol) was added at room temperature. After 1 h, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over sodium sulfate, filtrated, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 5-25% ethyl acetate/n-hexane gradient mixture to afford the desired product as pale yellow solid (65.5 mg, 0.170 mmol, 23%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with a 5-25% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-325426d0e6524bb4acd628cd514f4024
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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