Sodium Carbonate → HCID 118274412, compound

HRID 522204Notes

Reaction equation

HRID 522204 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([C:11]3[CH2:12][CH2:13][N:14]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:15][CH:16]=3)=[CH:10][C:3]=12.[F:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.COCCOC.O.C(O)C>[F:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[C:24]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[NH:8][C:9]([C:11]4[CH2:12][CH2:13][N:14]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:15][CH:16]=4)=[CH:10][C:3]=23)[CH:23]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 231525084-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 90412174HCID 90412174, compound

Product 1

HCID 118274412HCID 118274412, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Procedure

To a mixture of Example 5F (500 mg, 1.404 mmol), 4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (399 mg, 1.684 mmol) and dichlorobis(triphenylphosphine)palladium (II) (99 mg, 0.14 mmol) in 7:3:2 1,2-dimethoxyethane/water/ethanol (14 mL) was added 2.45 mL 2M aqueous sodium carbonate. The suspension was stirred at room temperature for a few seconds and then stirred in a microwave reactor (Biotage Initiator) at 150° C. for 30 minutes. The mixture was partitioned between ethyl acetate and brine and the organic phase was concentrated. The residue was stirred in 2% methanol in methylene chloride and the solid was collected by filtration to provide the title compound. The mother liquor was purified by flash chromatography on silica gel (Teledyne CombiFlash Rf, 0-15% methanol in dichloromethane) to provide additional title compound. MS (ESI+) m/z 387 (M+H)+.

Workup

  1. stirringstirred in a microwave reactor (Biotage Initiator) at 150° C. for 30 minutes
  2. customThe mixture was partitioned between ethyl acetate and brine
  3. concentrationthe organic phase was concentrated
  4. stirringThe residue was stirred in 2% methanol in methylene chloride
  5. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-c7a3d6840420461eac4847166f1c8d1b
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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