Sodium Carbonate → HCID 58547404, compound

HRID 1850251Notes

Reaction equation

HRID 1850251 reaction equation
Cl[C:2]1[C:3]([CH:8]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:15]([O:14][C:12]([N:10]1[CH2:11][CH:8]([C:3]2[C:2]([C:30]3[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:9]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 59351411Tert-butyl 3-(3-chloropyrazin-2-yl)azetidine-1-carboxylate

Product 1

HCID 58547404HCID 58547404, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-(3-chloro-pyrazin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (7) (100 mg, 0.37 mmol, as prepared in the above Preparation 2) in dioxane (8 mL) was added a solution of Na2CO3 (78 mg, 0.64 mmol) in 0.5 mL water, followed by additional of 4-methoxybenzeneboronic acid (20) (49 mg 0.40 mmol) and Pd(dppf)Cl2 (8 mg). The resulting mixture was heated to reflux overnight under N2 atmosphere. TLC showed that the starting material was consumed completely. The solution was filtered and the filtrate was concentrated to give the residue which was purified by column chromatography on silica gel to give the product compound (21) (120 mg, yield 96%) as solid. ESI-MS (M+1): 342 calc. for C19H23N3O3 341.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux overnight under N2 atmosphere
  3. customwas consumed completely
  4. filtrationThe solution was filtered
  5. concentrationthe filtrate was concentrated
  6. customto give the residue which
  7. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0966e5b1f5154fa2b2c7ef25c0f30bba
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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