Nitrogen → HCID 67957853, compound

HRID 919054Notes

Reaction equation

HRID 919054 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12](B3OC(C)(C)C(C)(C)O3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Br:24][C:25]1[CH:30]=[CH:29][C:28](I)=[CH:27][CH:26]=1.C(=O)(O)[O-].[Na+].N#N>COCCOC.O.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].CCOC(C)=O.O>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:28]3[CH:29]=[CH:30][C:25]([Br:24])=[CH:26][CH:27]=3)=[CH:13][CH:14]=2)[CH2:7][CH2:8]1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 947NitrogenHCID 115221-Bromo-4-iodobenzeneHCID 516892Sodium BicarbonateHCID 53217182Ethyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxylate

Product 1

HCID 67957853HCID 67957853, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 18180031Water 1,2-dimethoxyethaneSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
80 °C

Procedure

1-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester (2 g, 6.33 mmol), 1-bromo-4-iodo-benzene (1.97 g, 6.96 mmol), and sodium bicarbonate (1.59 g, 18.98 mmol) were dissolved in DME:H2O (2:1). The solution was sparged with N2 (g) for ten minutes then (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.52 g, 0.063 mmol) was added and N2 (g) was introduced for an additional 5 minutes. The reaction was heated to 80° C. for 4 hours then cooled and submitted to EtOAc/H2O workup. The crude material was purified on silica gel (0-70% EtOAc in hexanes) to provide the title compound.

Workup

  1. customThe solution was sparged with N2 (g) for ten minutes
  2. temperaturethen cooled
  3. customThe crude material was purified on silica gel (0-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-84cd09d306504cef91e8be2367c8fff4
Source dataset
uspto-grants-2016_03
Patent number
US09272990B2

Reaction notes

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