Sodium Carbonate → HCID 86723267, compound

HRID 1846048Notes

Reaction equation

HRID 1846048 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[CH:18][C:17]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:13]([S:10]([C:7]1[CH:6]=[C:3]([C:4]#[N:5])[C:2]([C:17]2[CH:18]=[C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[CH:20]=[CH:21][C:16]=2[F:15])=[CH:9][CH:8]=1)(=[O:12])=[O:11])[CH3:14]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 86723266HCID 86723266, compoundHCID 867232682-[2-Fluoro-5-[(4-methoxyphenyl)methoxy]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 86723267HCID 86723267, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
110 °C

Procedure

To 2-bromo-5-(ethylsulfonyl)benzonitrile (Preparation 75, 1.09 g, 3.96 mmol) in dioxane/water (5:1 v/v, 66 mL) was added 2-(2-fluoro-5-((4-methoxybenzyl)oxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 71, 1.56 g, 4.35 mmol) and sodium carbonate (1.26 g, 11.9 mmol). The reaction mixture was degassed and tetrakis(triphenylphosphine) palladium(0) (462 mg, 0.40 mmol) was added, and the reaction heated to 110° C. under nitrogen for 12 hours. After cooling to room temperature, silica gel was added, and the solvent removed under reduced pressure. The residue was purified using silica gel column chromatography eluting with EtOAc/cyclohexane 1:3 followed by reverse phase column chromatography eluting with MeCN/water, with 0.1% NH3 0-100% to afford the title compound as a solid in 51% yield, 851 mg.

Workup

  1. customThe reaction mixture was degassed
  2. temperatureAfter cooling to room temperature
  3. additionsilica gel was added
  4. customthe solvent removed under reduced pressure
  5. customThe residue was purified
  6. washeluting with EtOAc/cyclohexane 1:3
  7. washeluting with MeCN/water, with 0.1% NH3 0-100%

Sources & evidence

ORD record
ord-00eba72c76274a57baeb285aff67497d
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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