Phenylacetylene → 1-Isobutyl-6-phenylethynyl-1H-benzimidazol-2-ylamine

HRID 250760Notes

Reaction equation

HRID 250760 reaction equation
P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.C([O-])([O-])=O.[K+].[K+].Br[C:21]1[CH:22]=[CH:23][C:24]2[N:28]=[C:27]([NH2:29])[N:26]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:25]=2[CH:34]=1.[C:35]1([C:41]#[CH:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CS(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].[Cu]I>[CH2:30]([N:26]1[C:25]2[CH:34]=[C:21]([C:42]#[C:41][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:22]=[CH:23][C:24]=2[N:28]=[C:27]1[NH2:29])[CH:31]([CH3:33])[CH3:32]

Participants

8

Reactant 4

HCID 10821PhenylacetyleneHCID 11430Potassium CarbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 653467761-Isobutyl-2-amino-6-bromobenzimidazole

Product 1

HCID 668692771-Isobutyl-6-phenylethynyl-1H-benzimidazol-2-ylamineYield 60.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Heat a mixture of Pd(OAc)2 (1.25 g, 5.59 mmol), CuI (0.42 g, 2.23 mmol), P(t-Bu)3 (2.76 mL, 11.2 mmol), K2CO3 (30.3 g, 223.8 mmol) and 6-bromo-1-isobutyl-1H-benzimidazol-2-ylamine (30 g, 111.9 mmol) in DMSO (200 mL) at 70° C. Add phenylacetylene (14.6 mL, 133.4 mmol) and heat the mixture for 6 hours at 70° C. Cool and dilute with H20. Filter the residue through a pad of celite. Recrystallize the crude mixture in toluene to give the desired compound as a white solid (19.68 g, 60%).

Workup

  1. temperatureHeat
  2. temperatureCool
  3. additiondilute with H20
  4. filtrationFilter the residue through a pad of celite
  5. customRecrystallize the crude mixture in toluene

Sources & evidence

ORD record
ord-2f72b2442ebc437294069a615fa846b4
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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