Sodium Carbonate → HCID 89649075, compound

HRID 2207599Notes

Reaction equation

HRID 2207599 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:20]1([S:26]([CH:29]2[CH:39]([C:40]3[CH:45]=[C:44](Br)[CH:43]=[C:42]([CH3:47])[N:41]=3)[NH:38][C:31]3([CH2:35][CH2:34][N:33]([CH3:36])[C:32]3=[O:37])[CH2:30]2)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>COCCOC.O.O.CCOC(C)=O>[C:20]1([S:26]([CH:29]2[CH2:30][C:31]3([CH2:35][CH2:34][N:33]([CH3:36])[C:32]3=[O:37])[NH:38][CH:39]2[C:40]2[CH:45]=[C:44]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=3)[CH:43]=[C:42]([CH3:47])[N:41]=2)(=[O:28])=[O:27])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 89649142HCID 89649142, compound

Product 1

HCID 89649075HCID 89649075, compoundYield 103.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
120 °C

Procedure

PdCl2(Ph3P)2 (128.4 mg, 0.1800 mmol) was added to a degassed mixture of 4-trifluoromethylphenyl-boronic acid (365.03 mg, 1.92 mmol), sodium carbonate (582.01 mg, 5.49 mmol) and 7-(benzene-sulfonyl)-8-(4-bromo-6-methyl-2-pyridyl)-3-methyl-3,9-diazaspiro[4.4]nonan-4-one (which may be prepared as described in Description 12) (850 mg, 1.83 mmol) in DME (12 mL) and water (4 mL) under N2 in a microwave vial and the reaction was heated in the microwave at 120° C. for 1 hour. The mixture was diluted with water/EtOAc, filtered, and the phases separated. The organic layer was dried (Na2SO4) and the solvent evaporated to afford a light brown solid. This was purified using a Biotage SP4, 25 g SNAP cartridge, eluting with 0 to 10% MeOH/EtOAc to afford the 3-(benzenesulfonyl)-7-methyl-2-[6-methyl-4-[4-(trifluoromethyl)-phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]nonan-6-one (D16) (1 g, 1.8883 mmol) as an off-white solid (with traces of impurities);

Workup

  1. filtrationfiltered
  2. customthe phases separated
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvent evaporated
  5. customto afford a light brown solid
  6. customThis was purified
  7. washeluting with 0 to 10% MeOH/EtOAc

Sources & evidence

ORD record
ord-8e17bafb5aa74cafb14455ee6390899c
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

Loading…