Sodium Carbonate → HCID 58160174, compound

HRID 1879570Notes

Reaction equation

HRID 1879570 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][N:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>CCOCC.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>[CH2:19]([O:26][C:27]1[N:28]=[CH:29][C:30]([C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=2[N+:16]([O-:18])=[O:17])=[CH:31][CH:32]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 12027145HCID 12027145, compoundHCID 177502172-(Benzyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Product 1

HCID 58160174HCID 58160174, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of tert-butyl 4-chloro-3-nitrophenylcarbamate (818 mg, 3 mmol), 2-(benzyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (933 mg, 3 mmol), tetrakis(triphenylphosphine)palladium (104 mg, 0.09 mmol), 10 mL of dioxane, and 6 mL of 1 M Na2CO3 was heated at reflux for 15 h. It was diluted with 50 mL Et2O and washed with brine (2×50 mL) and dried over MgSO4 and concentrated. The crude product was purified by silica chromatography (EtOAc/hexane) to afford tert-butyl 4-(6-(benzyloxy)pyridin-3-yl)-3-nitrophenylcarbamate (WZ02049) as a yellow wax (1.2 g, 95%). MS (ESI) m/z 444 (M+Na+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 h
  3. washwashed with brine (2×50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by silica chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-dfe87d34b11d4c8ea2948404ec7375a8
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

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