Water → 3-Phenyl-9H-carbazole

HRID 1958274Notes

Reaction equation

HRID 1958274 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.O.C(=O)([O-])[O-].[K+].[K+].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl>[C:22]1([C:2]2[CH:3]=[CH:4][C:5]3[NH:6][C:7]4[C:12]([C:13]=3[CH:14]=2)=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 2524463-Bromocarbazole

Product 1

HCID 134974733-Phenyl-9H-carbazoleYield 90%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-bromo-9H-carbazole (0.4 g, 1.6 mmol) in DMF:H2O (15 mL:2 mL) are added tetrakis(triphenylphosphine)-palladium (0.184 g, 0.1 eq), potassium carbonate (0.66 g, 3 eq) and phenyl boronic acid (0.58 g, 3 eq). The resulting mixture is stirred at 80° C. for 4 hr. After cooling to rt, DCM (10 mL) is added and the reaction mixture is quenched with brine. After extraction, drying over MgSO4 and concentration in vacuo, the residue is purified via flash chromatography using PetEther:EtOAc 10:1 as eluting solvent to give the title compound (0.35 g, 1.44 mmol) as a white powder in a 90% yield. M.p.: 221° C.

Workup

  1. temperatureAfter cooling to rt
  2. customthe reaction mixture is quenched with brine
  3. extractionAfter extraction
  4. dry with materialdrying over MgSO4 and concentration in vacuo
  5. customthe residue is purified via flash chromatography
  6. washEtOAc 10:1 as eluting solvent

Sources & evidence

ORD record
ord-aa311ec51e694a0fbe857ff7d9acdcb6
Source dataset
uspto-grants-2013_04
Patent number
US08410110B2

Reaction notes

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