Water → HCID 58547347, compound

HRID 1850284Notes

Reaction equation

HRID 1850284 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[C:17](Br)=[CH:16][CH:15]=[CH:14][N:13]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.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:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:16][CH:15]=[CH:14][N:13]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27339503-Tolylboronic acidHCID 58546913HCID 58546913, compound

Product 1

HCID 58547347HCID 58547347, compoundYield 87.3%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3-(3-bromo-pyridin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (3) (150 mg, 0.48 mmol) in dioxane (10 mL) was added phenylboronic acid (78) (87 mg, 0.71 mmol), Na2CO3 (152 mg, 1.4 mmol) and H2O (2 mL). The reaction mixture was degassed with N2 and then PdCl2(dppf) (35 mg, 0.05 mmol) was added. The reaction mixture was stirred at 80° C. for 12 h. The reaction mixture was left to reach RT and filtered through a pad of CELITE® and the filter cake was washed with CH2Cl2 (20 mL×3). The combined filtrates were evaporated in vacuo and the residue was purified by column chromatography ((EtOAc:Petrol ether=3:1) to give the desired compound (79) (130 mg, 87% yield). ESI-MS (M+1): 311 calc. for C19H22N2O2 310.

Workup

  1. customThe reaction mixture was degassed with N2
  2. waitThe reaction mixture was left
  3. customto reach RT
  4. filtrationfiltered through a pad of CELITE®
  5. washthe filter cake was washed with CH2Cl2 (20 mL×3)
  6. customThe combined filtrates were evaporated in vacuo
  7. customthe residue was purified by column chromatography ((EtOAc:Petrol ether=3:1)

Sources & evidence

ORD record
ord-829bce7c28494257b79a41f5b5a19406
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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