Potassium Phosphate, Tribasic → US10023592, Example 237

HRID 575713Notes

Reaction equation

HRID 575713 reaction equation
Br[C:2]1[C:3]2[O:12][CH:11]=[N:10][C:4]=2[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[CH:13]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][C:19]=2B2OC(C)(C)C(C)(C)O2)[CH2:15][CH2:14]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:13]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][C:19]=2[C:2]2[C:3]3[O:12][CH:11]=[N:10][C:4]=3[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=2)[CH2:14][CH2:15]1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 847260897-Bromo-5-methyl-[1,3]oxazolo[4,5-c]pyridin-4-oneHCID 1234348592-[2-(Cyclopropylmethoxy)-5-(methylsulfonyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 118022201US10023592, Example 237Yield 20%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

The title compound of step 5 (60 mg, 0.3 mmol) in dioxane (2 mL) and H2O (0.4 mL) was stirred at 15° C. under N2 for 30 min. Pd(dppf)Cl2 (19 mg, 0.026 mmol), the title compound of Example 90, step 1 (120 mg, 0.3 mmol) and K3PO4 (166 mg, 0.8 mmol,) were added at 15° C. under N2. The reaction mixture was heated at 60° C. for 12 h. Purification by silica gel chromatography (EA) and preparative HPLC gave the title compound (20.63 mg, 20%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.03 (d, J=2.0 Hz, 1H), 8.02 (s, 1H), 7.96 (dd, J1=8.4 Hz, J2=2.0 Hz, 1H), 7.09 (d, J=8.4 Hz, 1H), 3.96 (d, J=6.8 Hz, 2H), 3.76 (s, 3H), 3.1 (s, 3H), 1.18 (m, 1H), 0.60 (m, 2H), 0.30 (m, 2H). LCMS: 375.1 (M+H)+

Workup

  1. customPurification by silica gel chromatography (EA) and preparative HPLC

Sources & evidence

ORD record
ord-aebff3f5ba534308b25dbd48a1852add
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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