Sodium Carbonate → HCID 59526001, compound

HRID 386150Notes

Reaction equation

HRID 386150 reaction equation
I[C:2]1[S:6][C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=2)=[C:4]([C:15]([NH2:17])=[O:16])[CH:3]=1.[CH3:18][N:19]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[N:20]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:18][N:19]1[CH:23]=[C:22]([C:2]2[S:6][C:5]([NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=3)=[C:4]([C:15]([NH2:17])=[O:16])[CH:3]=2)[CH:21]=[N:20]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 59525912HCID 59525912, compound

Product 1

HCID 59526001HCID 59526001, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 5-iodo-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide (300 mg, 0.84 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (619 mg, 2.97 mmol), dichlorobis(triphenylphosphine)palladium (29.3 mg, 0.04 mmol), and sodium carbonate (7.5 mL, 15.0 mmol) in 1,2-dimethoxyethane (7.5 mL) sealed in a 20 mL microwave reaction vessel was purged of oxygen by doing 5 vacuum/argon flush cycles. The reaction solution was heated in a microwave for five minutes at 100° C., and then partitioned between ethyl acetate (50 mL) and water (30 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography (12-100% ethyl acetate/hexanes) yielded the title compound.

Workup

  1. customsealed in a 20 mL microwave reaction vessel
  2. customwas purged of oxygen
  3. customflush cycles
  4. custompartitioned between ethyl acetate (50 mL) and water (30 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (50 mL)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by silica gel chromatography (12-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-aef4b49e245e4b62893891ce3083e742
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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