Potassium Phosphate, Tribasic → US10023592, Example 259

HRID 518474Notes

Reaction equation

HRID 518474 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[C:5]2[CH:17]=[CH:18][O:19][C:4]=2[C:3]1=[O:20].[CH:21]1([CH2:24][O:25][C:26]2[C:27](I)=[N:28][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:30][CH:31]=2)[CH2:23][CH2:22]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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:21]1([CH2:24][O:25][C:26]2[C:27]([C:6]3[C:5]4[CH:17]=[CH:18][O:19][C:4]=4[C:3](=[O:20])[N:2]([CH3:1])[CH:7]=3)=[N:28][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:30][CH:31]=2)[CH2:22][CH2:23]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 1180225163-(Cyclopropylmethoxy)-2-iodo-6-methylsulfonylpyridineHCID 1240169906-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furo[2,3-c]pyridin-7-one

Product 1

HCID 118021483US10023592, Example 259Yield 62.3%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
70 °C

Procedure

A mixture of 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furo[2,3-c]pyridin-7-one (50 mg, 0.18 mmol), 3-(cyclopropylmethoxy)-2-iodo-6-methylsulfonylpyridine (53 mg, 0.15 mmol), K3PO4 (114 mg, 0.54 mmol), Pd(dppf)Cl2 (13 mg, 0.018 mmol) in dioxane (5 mL) was bubbled with nitrogen for 5 min and then stirred at 70° C. for 12 h. The reaction mixture was concentrated, treated with DCM (30 mL), washed with water (30 mL) and brine (30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by prep-HPLC to give the title compound (35 mg, yield: 52%) as an off-white solid.

Workup

  1. customwas bubbled with nitrogen for 5 min
  2. concentrationThe reaction mixture was concentrated
  3. additiontreated with DCM (30 mL)
  4. washwashed with water (30 mL) and brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-c39d564df8e24039aa2f0c6799d6331d
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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