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

HRID 1994166Notes

Reaction equation

HRID 1994166 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1I)=[O:7])([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]([NH:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:19]1[CH:20]=[CH:21][C:16]([Br:15])=[CH:17][CH:18]=1)=[O:7])([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 (tert-Butoxy)-N-(2-iodo(3-thiophenyl))carboxamide (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. Evaporate the organic solvents prior to the addition of water (200 mL). Extract the mixture with methylene chloride (3×150 mL) and combine the organic phases, dry (anh MgSO4), filter, and concentrate to furnish a crude mixture as a yellowish solid. Purification by flash chromatography (Silica gel-Hexane/EtOAc 49:1) yields 10.8 g (60%) of (tert-butoxy)-N-[2-(4-bromophenyl)(3-thiophenyl)]carboxamide 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 methylene chloride (3×150 mL)
  5. dry with materialdry (anh MgSO4)
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto furnish a crude mixture as a yellowish solid
  9. customPurification by flash chromatography (Silica gel-Hexane/EtOAc 49:1)

Sources & evidence

ORD record
ord-0fa28f56690b4865b88e28e19fb40416
Source dataset
uspto-grants-2010_01
Patent number
US07652064B2

Reaction notes

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