Sodium Carbonate → HCID 90412095, compound

HRID 1521984Notes

Reaction equation

HRID 1521984 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:9]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)=[CH:10][C:3]=12.[F:34][C:35]1[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:34][C:35]1[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=1[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:24]([C:27]3[CH:28]=[CH:29][C:30]([CH3:31])=[CH:32][CH:33]=3)(=[O:26])=[O:25])[C:9]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:13][CH:12]=3)=[CH:10][C:3]=12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734333(2,3-Difluorophenyl)boronic acidHCID 90409204HCID 90409204, compound

Product 1

HCID 90412095HCID 90412095, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Procedure

A mixture of Example 220C (750.0 mg, 1.409 mmol), (2,3-difluorophenyl)boronic acid (267 mg, 1.690 mmol), bis(triphenylphosphine)palladium(II)dichloride (39.5 mg, 0.056 mmol), and 1M sodium carbonate (1409 μL, 1.409 mmol) in 10 mL 1,2-dimethoxyethane/ethanol/water (7:2:3) was heated in a Biotage Initiator microwave reactor at 150° C. for 15 minutes. The mixture was concentrated, treated with ethyl acetate and washed with aqueous sodium bicarbonate. The organic layer was washed with water, dried over magnesium sulfate, filtered, concentrated and purified on silica gel using an ISCO Companion eluting with heptanes/ethyl acetate (7:3 to 6:4) to give the title compound. MS (ESI+) m/z 566.1 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. additiontreated with ethyl acetate
  3. washwashed with aqueous sodium bicarbonate
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified on silica gel using an ISCO Companion
  9. washeluting with heptanes/ethyl acetate (7:3 to 6:4)

Sources & evidence

ORD record
ord-c08ebd22c6384d20a1cf9da25a7449bb
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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