Potassium Phosphate, Tribasic → HCID 117667278, compound

HRID 712624Notes

Reaction equation

HRID 712624 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[N:16][CH:17]=2)[N:14]([C:18]([NH2:20])=[O:19])[CH2:13][CH2:12][CH2:11]3)[CH:5]=[N:6][CH:7]=1.O1CCOCC1.O.CC1(C)C(C)(C)OB([C:36]2[CH2:37][CH2:38][O:39][CH2:40][CH:41]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CCOC(C)=O>[O:39]1[CH2:38][CH:37]=[C:36]([C:2]2[CH:3]=[C:4]([C:8]3[CH:9]=[C:10]4[C:15](=[N:16][CH:17]=3)[N:14]([C:18]([NH2:20])=[O:19])[CH2:13][CH2:12][CH2:11]4)[CH:5]=[N:6][CH:7]=2)[CH2:41][CH2:40]1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 218864351,4-Dioxane--water (1/1)HCID 117667498HCID 117667498, compound

Product 1

HCID 117667278HCID 117667278, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

6-(5-Bromo-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (100 mg, 0.30 mmol, which is prepared according to the procedure for Step 1 to Step 4 of Example 15) is dissolved into 2 mL of dioxane/water (9:1). 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (94.6 mg, 0.45 mmol), K3PO4 (318 mg, 1.50 mmol) and PdCl2(DPPF)CH2Cl2 (24.5 mg, 0.03 mmol) are added. The mixture is heated at 100° C. for 48 hrs. The mixture is diluted with 100 mL EtOAc and quenched with 100 mL of saturated aqueous NH4Cl. The organic phase is washed with 2×20 mL of H2O and 1×20 mL of brine. The organic phase is dried with MgSO4, filtered and concentrated. The crude material is applied to a silica preparative TLC plate and purified twice to give 52.1 mg of the titled product.

Workup

  1. customquenched with 100 mL of saturated aqueous NH4Cl
  2. washThe organic phase is washed with 2×20 mL of H2O and 1×20 mL of brine
  3. dry with materialThe organic phase is dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified twice

Sources & evidence

ORD record
ord-cbc5a7851fd3416e85b2e3b8f70b03ae
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

Loading…