Sodium Hydroxide → HCID 57543436, compound

HRID 2261250Notes

Reaction equation

HRID 2261250 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9](B2OC(C)(C)C(C)(C)O2)[C:10]=1[CH3:11])[C:5]([NH2:7])=[O:6].Br[C:22]1[C:27](=[O:28])[N:26]([CH3:29])[C:25]2[N:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:39])[N:31]=[CH:32][C:24]=2[CH:23]=1.[OH-].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[Cl:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[N:30]1[C:25]2[N:26]([CH3:29])[C:27](=[O:28])[C:22]([C:9]3[CH:8]=[C:4]([CH:3]=[C:2]([F:1])[C:10]=3[CH3:11])[C:5]([NH2:7])=[O:6])=[CH:23][C:24]=2[CH:32]=[N:31]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 46197587HCID 46197587, compoundHCID 68739307HCID 68739307, compound

Product 1

HCID 57543436HCID 57543436, compoundYield 88.7%

Reagents, catalysts & solvents 3

HCID 10340Sodium CarbonateCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (118 mg, 422 μmol), 5-bromo-1-(2-chlorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (130 mg, 384 μmol), Pd(PPh3)4 (0.016 mmol, 19 mg), and sodium carbonate (2 M) (0.576 ml, 1.15 μmol) in 2.0 mL of dioxane in a sealed tube was heated in a microwave at 125° C. for 25 min. The mixture was treated with 2 mL of 1 N NaOH solution, extracted with 2×5 mL of EtOAc. The combined organic phases were washed with 2 mL of brine, dried and concentrated. The brown residue was loaded on an ISCO 12 g column (eluting with a gradient of 1-6% MeOH in DCM) to provide the title compound (140 mg) as an off white crystalline solid. MS (ESI, pos.ion) m/z: 411.2 (M+1).

Workup

  1. extractionextracted with 2×5 mL of EtOAc
  2. washThe combined organic phases were washed with 2 mL of brine
  3. customdried
  4. concentrationconcentrated
  5. washeluting with a gradient of 1-6% MeOH in DCM)

Sources & evidence

ORD record
ord-25cedf0c1ff34c23881c52aac2af7e69
Source dataset
uspto-grants-2010_12
Patent number
US07846944B2

Reaction notes

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