Sodium Carbonate → tert-Butyl [2-(4-bromophenyl)thiophen-3-yl]carbamate

HRID 1990063Notes

Reaction equation

HRID 1990063 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1[CH:12]=[CH:11][S:10][C:9]=1I)([CH3:4])([CH3:3])[CH3:2].[Br:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>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>[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1[CH:12]=[CH:11][S:10][C:9]=1[C:19]1[CH:20]=[CH:21][C:16]([Br:15])=[CH:17][CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 79599(4-Bromophenyl)boronic acidHCID 11034707TERT-BUTYL 2-IODOTHIOPHEN-3-YLCARBAMATE

Product 1

HCID 57975436tert-Butyl [2-(4-bromophenyl)thiophen-3-yl]carbamateYield 60%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Heat (2-iodo-thiophen-3-yl)-carbamic acid tert-butyl ester (16.88 g, 0.52 mol), 4-bromophenylboronic acid (15.65 g, 0.78 mol), Na2CO3 (1.01 g, 1.04 mol) and Pd(PPh3)4 (5.79 g, 0.052 mol) in 375 ml of an anhydrous and deoxygenated 2:1 DME/EtOH mixture to 80° C. under nitrogen atmosphere for 24 h. Anaylsis by T.L.C. (Hexane/Ethyl acetate 9:1) shows complete disapperence of starting material. Evaporate the organic solvents, prior to the addition of water (200 mL). Extract the mixture with dichloromethane (3×150 mL) and dry the combined organic phases (MgSO4) and concentrate to furnish a crude mixture as a yellowish solid. Purification by flash chromatography (Silica gel-Hexane/Ethyl acetate 49:1) yielded 10.8 g (60%) of title compound as a pale yellow solid.

Workup

  1. customdeoxygenated 2:1 DME/EtOH mixture to 80° C. under nitrogen atmosphere for 24 h
  2. customEvaporate the organic solvents
  3. additionto the addition of water (200 mL)
  4. extractionExtract the mixture with dichloromethane (3×150 mL)
  5. dry with materialdry the combined organic phases (MgSO4)
  6. concentrationconcentrate
  7. customto furnish a crude mixture as a yellowish solid
  8. customPurification by flash chromatography (Silica gel-Hexane/Ethyl acetate 49:1)

Sources & evidence

ORD record
ord-81fa610404034ad8997ce685a298746c
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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