Sodium Carbonate → HCID 70872705, compound

HRID 1959261Notes

Reaction equation

HRID 1959261 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:25](=[O:37])[NH:26][CH2:27][C:28]2[C:29](=[O:36])[NH:30][C:31]([CH3:35])=[CH:32][C:33]=2[CH3:34])[C:5]([CH3:24])=[C:6]([N:8]([CH2:22][CH3:23])[CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:7]=1.B(O)O.C([O-])([O-])=O.[Na+].[Na+].O1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1.O>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>[CH3:34][C:33]1[CH:32]=[C:31]([CH3:35])[NH:30][C:29](=[O:36])[C:28]=1[CH2:27][NH:26][C:25]([C:4]1[C:5]([CH3:24])=[C:6]([N:8]([CH2:22][CH3:23])[CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[CH2:13][CH2:14]2)[CH:7]=[C:2]([C:7]2[CH:6]=[CH:5][C:4]([CH2:25][N:26]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)=[CH:3][CH:2]=2)[CH:3]=1)=[O:37]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 218864351,4-Dioxane--water (1/1)HCID 70872611HCID 70872611, compound

Product 1

HCID 70872705HCID 70872705, compoundYield 68.66%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of tert-butyl 4-((5-bromo-3-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-2-methyl-phenyl)(ethyl)amino)piperidine-1-carboxylate (2 g, 3.47 mmol) and 4-(morpholinomethyl)-phenyl)boronic acid (1.58 g, 5.21 mmol) in dioxane/water mixture, Na2CO3 (1.32 g, 12.45 mmol) was added and solution purged with argon for 15 min. Then Pd (PPh3)4 (0.4 g, 0.35 mmol) was added and argon was purged again for 10 min. The reaction mixture was heated at 90° C. for 3.5 h. On completion, reaction mixture was diluted with water and extracted with 10% MeOH/DCM. Combined organic layers were dried over Na2SO4 and solvent removed under reduced pressure to afford crude material which was purified by column chromatography over silica gel to afford desired compound (1.6 g, 68.66%).

Workup

  1. customsolution purged with argon for 15 min
  2. customargon was purged again for 10 min
  3. customOn completion, reaction mixture
  4. extractionextracted with 10% MeOH/DCM
  5. dry with materialCombined organic layers were dried over Na2SO4 and solvent
  6. customremoved under reduced pressure
  7. customto afford crude material which
  8. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-bae884c6b64c43159a7f17c9b7f20f86
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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