2,6-Dichloro-4-iodopyridine → HCID 178521586, compound

HRID 390099Notes

Reaction equation

HRID 390099 reaction equation
Cl[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[NH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]1.CN(C)C=O.O1CCOCC1>C(OCC)(=O)C>[Cl:9][C:4]1[N:3]=[C:2]([NH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]2)[CH:7]=[C:6]([I:8])[CH:5]=1

Participants

5

Reactant 3

HCID 117373932,6-Dichloro-4-iodopyridineHCID 217120691,4-dioxane N,N-dimethylformamideHCID 178511715HCID 178511715, compound

Product 1

HCID 178521586HCID 178521586, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

A suspension of 2,6-dichloro-4-iodopyridine (6 g, 21.9 mmol) and trans 4-aminocyclohexanol (5.05 g, 43.8 mmol) in 15 mL of a 1:4 mixture of N,N-dimethylformamide/1,4-dioxane was heated in a Biotage Initiator microwave at 200° C. for 55 min. Ethyl acetate (150 mL) was added and the mixture washed with water (100 mL) and brine (50 mL). The organics were concentrated and the residue purified by flash chromatography on silica gel eluting with 60% ethyl acetate in hexanes to provide the title compound. Yield: 3.8 g (49%). MS (DCI/NH3) m/z 353 (M+H)+.

Workup

  1. washthe mixture washed with water (100 mL) and brine (50 mL)
  2. concentrationThe organics were concentrated
  3. customthe residue purified by flash chromatography on silica gel eluting with 60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ea5fd68668aa410da698ba58d0fdb722
Source dataset
uspto-grants-2013_02
Patent number
US08383624B2

Reaction notes

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