Sodium Carbonate → HCID 58406076, compound

HRID 218009Notes

Reaction equation

HRID 218009 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([N:25]([C:33]1[S:42][CH2:41][C@H:40]2[C@:35]([C:43]3[CH:48]=[C:47](Br)[CH:46]=[CH:45][C:44]=3[F:50])([CH2:36][O:37][CH2:38][CH2:39]2)[N:34]=1)C(OC(C)(C)C)=O)(=O)C1C=CC=CC=1>CN(C=O)C.O.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:50][C:44]1[CH:45]=[CH:46][C:47]([C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:48][C:43]=1[C@@:35]12[N:34]=[C:33]([NH2:25])[S:42][CH2:41][C@@H:40]1[CH2:39][CH2:38][O:37][CH2:36]2

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 58405994HCID 58405994, compound

Product 1

HCID 58406076HCID 58406076, compoundYield 38.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-Fluoropyridine-3-boronic acid (25.6 mg), tetrakis(triphenylphosphine)palladium (10.5 mg) and a 1 N sodium carbonate solution (182 μl ) were added to a solution of (±)-N-benzoyl-N-(tert-butyloxycarbonyl)-[(4aR*,8aS*)-8a-(5-bromo-2-fluorophenyl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]amine (50 mg) in DMF (5.0 ml). After replacement with nitrogen, the mixture was stirred at 90° C. for six hours. The reaction solution was cooled to room temperature and diluted with water. The aqueous layer was extracted with ethyl acetate. 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 (12.7 mg).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-d2279088302540609ce12f4cf49655f1
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

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