Triethylamine → HCID 67050128, compound

HRID 1875818Notes

Reaction equation

HRID 1875818 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:13]([CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[C:12]2[CH:21]=[C:22]([F:26])[C:23]([F:25])=[CH:24][C:11]=2[N:10]=1.[C:27]([C:29]1[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=1)#[CH:28].C(N(CC)CC)C>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]2[N:13]([CH2:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:12]3[CH:21]=[C:22]([F:26])[C:23]([F:25])=[CH:24][C:11]=3[N:10]=2)=[C:2]([C:28]#[C:27][C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 45472454-EthynylbenzonitrileHCID 67049952HCID 67049952, compound

Product 1

HCID 67050128HCID 67050128, compoundYield 18%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(2-bromo-4-chloro-phenyl)-1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazole (600 mg, 1.36 mmol) in tetrahydrofuran (20 ml) was added 4-ethynyl-benzonitrile (173.4 mg, 1.36 mmol; CAS Reg. No. 3032-92-6), bis(triphenylphosphine)palladium(ii) dichloride (57.2 mg, 0.08 mmol), copper iodide (7.7 mg, 0.04 mmol) and triethyl amine (20 ml) at 25° C. The resulting mixture was degassed and back-filled with nitrogen three times. It was then allowed to stir at 80° C. for 16 h. The reaction mixture was filtered through a bed of celite and solvents were removed under reduced pressure. The residue was purified by column chromatography over silica gel (10% ethyl acetate/n-hexane) to afford the desired compound as a yellow solid (18%). MS (Turbo Spray): m/z=485.6 (M+H).

Workup

  1. customat 25° C
  2. customThe resulting mixture was degassed
  3. additionback-filled with nitrogen three times
  4. filtrationThe reaction mixture was filtered through a bed of celite and solvents
  5. customwere removed under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel (10% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-af5a06b9c7c64ebe90dd8122daa56ab9
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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