Triethylamine → [4-(1H-benzimidazol-2-yl)piperidin-1-yl](5-bromopyridin-2-yl)methanone

HRID 1913150Notes

Reaction equation

HRID 1913150 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.Cl.Cl.[NH:13]1[CH2:18][CH2:17][CH:16]([C:19]2[NH:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[N:20]=2)[CH2:15][CH2:14]1.Cl.C(N=C=N)C.C(N(CC)CC)C>ClC(Cl)C.CN(C)C1C=CN=CC=1>[NH:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[CH:16]1[CH2:17][CH2:18][N:13]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[O:10])[CH2:14][CH2:15]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 6085445-Bromopyridine-2-carboxylic acidHCID 21883477Ethylcarbodiimide hydrochlorideHCID 450738062-(piperidin-4-yl)-1H-benzimidazole dihydrochloride

Product 1

HCID 58494556[4-(1H-benzimidazol-2-yl)piperidin-1-yl](5-bromopyridin-2-yl)methanoneYield 14%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred mixture of 5-bromopyridine-2-carboxylic acid (177 mg, 0.88 mmol) and 2-(piperidin-4-yl)-1H-benzimidazole dihydrochloride (200 mg, 0.73 mmol) in dichloroethane (5 mL) is added ethylcarbodiimide hydrochloride (168 mg, 0.88 mmol), triethylamine (0.25 mL, 1.82 mmol) and 4-dimethylaminopyridine (44.6 mg, 0.36 mmol). After 3 h the reaction mixture is washed with saturated aqueous NaHCO3, water and brine. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure. Trituration from hot EtOAc gives 39.4 mg of [4-(1H-benzimidazol-2-yl)piperidin-1-yl](5-bromopyridin-2-yl)methanone.

Workup

  1. washAfter 3 h the reaction mixture is washed with saturated aqueous NaHCO3, water and brine
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2f0ceccfa4b24f44ad7d7b34e5f88c48
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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