Sodium Carbonate → HCID 89649354, compound

HRID 2207621Notes

Reaction equation

HRID 2207621 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.[CH2:19]([O:21][C:22]1[CH:23]=[CH:24][C:25]([F:31])=[C:26](B(O)O)[CH:27]=1)[CH3:20].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>[CH2:19]([O:21][C:22]1[CH:23]=[CH:24][C:25]([F:31])=[C:26]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]3[CH2:12][CH2:11][C@:10]4([CH2:16][CH2:15][N:14]([CH3:17])[C:13]4=[O:18])[N:9]=3)[CH:3]=2)[CH:27]=1)[CH3:20]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 162174685-Ethoxy-2-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 89649281HCID 89649281, compound

Product 1

HCID 89649354HCID 89649354, compoundYield 100.4%

Reagents, catalysts & solvents 3

HCID 178419050HCID 178419050, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (5R)-2-(4-bromo-pyridin-2-yl)-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one (which may be prepared as described in Description 3) (0.1670 g, 0.5419 mmol) in MeCN (2 mL) and water (0.3000 mL) in a Smith microwave vessel was added (5-ethoxy-2-fluoro-phenyl)boronic acid (0.1097 g, 0.5961 mmol), bis(triphenylphosphine)palladium (II) dichloride (0.0114 g, 0.0163 mmol) and sodium carbonate (0.1149 g, 1.0838 mmol). The reaction vessel was sealed and purged with nitrogen. The reaction mixture was heated by microwave at 100° C. for 40 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. Evaporation of solvents gave an amber oil, which was further purified by silica gel chromatography to give the desired product (5R)-2-[4-(5-ethoxy-2-fluoro-phenyl)-2-pyridyl]-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one (0.2000 g, 0.5443 mmol) (D55) as an amber oil;

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. customEvaporation of solvents
  7. customgave an amber oil, which
  8. customwas further purified by silica gel chromatography

Sources & evidence

ORD record
ord-39d2148663b24f49aacc8c24800cdfbf
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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