Sodium Carbonate → HCID 89649163, compound

HRID 2207655Notes

Reaction equation

HRID 2207655 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH2:12][CH2:11][C@@:10]3([CH2:16][CH2:15][N:14]([CH3:17])[C:13]3=[O:18])[N:9]=2)[CH:3]=1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC#N.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:17][N:14]1[CH2:15][CH2:16][C@:10]2([N:9]=[C:8]([C:4]3[CH:3]=[C:2]([C:24]4[CH:25]=[CH:26][C:21]([C:20]([F:31])([F:30])[F:19])=[CH:22][CH:23]=4)[CH:7]=[CH:6][N:5]=3)[CH2:12][CH2:11]2)[C:13]1=[O:18]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 89649250HCID 89649250, compound

Product 1

HCID 89649163HCID 89649163, compoundYield 89.6%

Reagents, catalysts & solvents 3

HCID 178419050HCID 178419050, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (5S)-2-(4-bromo-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one (which may be prepared as described in Description 3) (640 mg, 2.0768 mmol) in MeCN (8 mL) and water (1 mL) in a Smith microwave vessel was added [4-(trifluoromethyl)-phenyl]boronic acid (394.44 mg, 2.0768 mmol), bis(triphenylphosphine)palladium (II) dichloride (60 mg, 0.0855 mmol) and sodium carbonate (484.26 mg, 4.5689 mmol). The reaction vessel was sealed and purged with nitrogen. The reaction mixture was heated by microwave at 120° C. for 25 min. The reaction mixture was treated with water and was extracted with DCM twice and the organic layers were collected by passing down a PhaseSep cartridge, and evaporated. The crude residue was purified by silica gel chromatography (50 g, SiO2) eluting with ethyl acetate in iso-hexane (10-100%). Evaporation of desired fractions gave (5S)-7-methyl-2-[4-[4-(trifluoromethyl)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]non-1-en-6-one (D118) (695 mg, 1.8614 mmol, 89.6% yield);

Workup

  1. customThe reaction vessel was sealed
  2. custompurged with nitrogen
  3. additionThe reaction mixture was treated with water
  4. extractionwas extracted with DCM twice
  5. customthe organic layers were collected
  6. customevaporated
  7. customThe crude residue was purified by silica gel chromatography (50 g, SiO2)
  8. washeluting with ethyl acetate in iso-hexane (10-100%)
  9. customEvaporation of desired fractions

Sources & evidence

ORD record
ord-aa9fcdd5de1c4b2bbbe4ac7124168b88
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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