3-Butyn-1-OL → HCID 11461663, compound

HRID 644548Notes

Reaction equation

HRID 644548 reaction equation
I[C:2]1[C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.[CH2:21]([OH:25])[CH2:22][C:23]#[CH:24].[Cl-].[NH4+]>N1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[OH:25][CH2:21][CH2:22][C:23]#[C:24][C:2]1[C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1

Participants

7

Reactant 3

HCID 135663-Butyn-1-OLHCID 25517Ammonium ChlorideHCID 194260247-Iodo-1-phenyl-5-(trifluoromethyl)-1H-benzimidazole

Product 1

HCID 11461663HCID 11461663, compoundYield 164.7%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 31268PyrrolidineSolvent2×

Conditions

Temperature
75 °C

Procedure

To a stirred solution of 7-iodo-1-phenyl-5-trifluoromethylbenzimidazole (9.7 g, 25 mmol) and tetrakis(triphenylphosphine)palladium(0) (2.9 g, 5 mmol) in pyrrolidine (75 ml) was added a solution of 3-butyn-1-ol (7.0 g, 0.1 mol) in pyrrolidine (75 ml), then copper (I) iodide (475 mg, 2.5 mmol). The resulting solution was heated to 75° C. with stirring under nitrogen. After 2.5 h the reaction mixture was allowed to cool, treated with saturated aqueous ammonium chloride and extracted with diethyl ether. The combined organic extracts were dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to leave a residue (13.6 g). This residue was flash chromatographed over silica gel (eluted with dichloromethane/diethyl ether 4:1) to give the desired product (3.95 g, 48%) m/z, 330.8 (M+H)+.

Workup

  1. temperatureto cool
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulphate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-bec3fca9864a45ebbd9a98782ec21124
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

Loading…