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Water → HCID 58547347, compound

HRID 1850290
Notes
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Reaction equation

HRID 1850290 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

HCID 58547347HCID 58547347, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 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) (158 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 3-(3-phenyl-pyridin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (125 mg, 0.38 mmol, 80% yield).

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-8823f7d4bc3743548995016fabf2954f
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957073B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes