2-Bromopyridine → HCID 57415343, compound

HRID 533167Notes

Reaction equation

HRID 533167 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[N:11][C:12]2[CH2:13][CH2:14][NH:15][C:16](=[O:19])[C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cu]I>[CH2:1]([O:8][C:9]1[CH:10]=[N:11][C:12]2[CH2:13][CH2:14][N:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:16](=[O:19])[C:17]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 68008654HCID 68008654, compound

Product 1

HCID 57415343HCID 57415343, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

3-(Benzyloxy)-7,8-dihydro-1,6-naphthyridin-5(6H)-one, example 1.15, (10.0 mg, 0.04 mmol), 2-bromopyridine (8.0 μL, 0.08 mmol), CuI (1.1 mg, 0.006 mmol) and K2CO3 (11.0 mg, 0.08 mmol) were mixed in DMF (0.5 mL), and heated to 150° C. for 2 days. The reaction was partitioned between EtOAc (10 mL) and brine (10 mL). The organics were dried and concentrated and purified by RP-HPLC to afford the compound. LC-MS (M+H)=332.1.

Workup

  1. customThe reaction was partitioned between EtOAc (10 mL) and brine (10 mL)
  2. customThe organics were dried
  3. concentrationconcentrated
  4. custompurified by RP-HPLC
  5. customto afford the compound

Sources & evidence

ORD record
ord-b6071ff833dc4591903a930296b19e54
Source dataset
uspto-grants-2014_10
Patent number
US08853237B2

Reaction notes

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