Ethyl Acetate → HCID 57827206, compound

HRID 1842283Notes

Reaction equation

HRID 1842283 reaction equation
[F:1][C:2]1[C:7](B(O)O)=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OC([N:24]([C:33]1[S:42][CH2:41][C@H:40]2[C@:35]([C:43]3[S:44][CH:45]=[C:46](Br)[CH:47]=3)([CH2:36][CH2:37][O:38][CH2:39]2)[N:34]=1)C(=O)C1C=CC=CC=1)=O)(C)(C)C.C(OCC)(=O)C>CN(C=O)C.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>[F:1][C:2]1[C:7]([C:46]2[CH:47]=[C:43]([C@@:35]34[N:34]=[C:33]([NH2:24])[S:42][CH2:41][C@@H:40]3[CH2:39][O:38][CH2:37][CH2:36]4)[S:44][CH:45]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 57827385HCID 57827385, compound

Product 1

HCID 57827206HCID 57827206, compoundYield 36.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-Fluoropyridine-3-boronic acid (15.7 mg), tetrakis(triphenylphosphine)palladium (4.3 mg) and a 1 N sodium carbonate solution (112 μL) were added to a solution of (±)-N-tert-butoxycarbonyl-N-[(4aS*,8aS*)-8a-(4-bromo-thiophen-2-yl)-4a,7,8,8a-tetrahydro-4H,5H-6-oxa-3-thia-1-azanaphthalen-2-yl]benzamide (20.0 mg) in DMF (1 mL). After replacement with nitrogen, the mixture was stirred at 90° C. for seven hours. After cooling to room temperature, ethyl acetate was added to the reaction mixture. The organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by NH-silica gel column chromatography to obtain the title compound (4.7 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-0cc6fdb3440c443dac8aed2956330d3a
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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