2-Bromopyridine → HCID 49872841, compound

HRID 80258Notes

Reaction equation

HRID 80258 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][NH:12][C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=4)[C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Product 1

HCID 49872841HCID 49872841, compoundYield 18.13%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

1-Benzothiazol-6-yl-imidazolidin-2-one (I-84b: 150 mg, 0.6904 mmol) was reacted with 2-bromo-pyridine (99 mL, 1.0356 mmol), 1,4-dioxane (10 mL), copper iodide (16 mg), trans-1,2-diamino cyclohexane (32 mg) and potassium phosphate (440 mg, 2.0713 mmol) to afford the crude product. Purification by column chromatography on silica gel (10% ethylacetate in hexane), followed by preparative HPLC afforded 37 mg of the product (18.13% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (10% ethylacetate in hexane)

Sources & evidence

ORD record
ord-413807e3525c4bc1bc895f470ee214be
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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