Tetrahydrofuran → HCID 592582, compound

HRID 1428827Notes

Reaction equation

HRID 1428827 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1(B(O)O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1I.C1COCC1>C(Cl)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].Cl[Pd]Cl>[Cl:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 966402-Chloro-1-iodo-4-nitrobenzene

Product 1

HCID 592582HCID 592582, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of potassium carbonate (1.48 g, 10.7 mmol), phenylboronic acid (645 mg, 5.29 mmol), 3-chloro-4-iodonitro benzene (1.00 g, 3.53 mmol), and THF (31 ml) was degassed with nitrogen in a sealable tube for 10 min. The dichloromethane adduct of 1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium (351 mg, 0.429 mmol) was added to the reaction mixture and the pressure tube was sealed. The reaction mixture was stirred at 100° C. for 42 h. The mixture was cooled to 23° C., diluted with DCM (40 ml), and filtered. The filtrate was concentrated. The residue was purified by FCC (3-50% EtOAc/hexanes) to yield the titled compound (796 mg, 97%). 1H NMR (600 MHz, DMSO-d6): 8.42-8.41 (m, 1H), 8.26 (dd, J=8.5, 2.2, Hz 1H), 7.72 (d, J=8.5 Hz, 1H), 7.55-7.48 (m, 5H).

Workup

  1. customwas degassed with nitrogen in a sealable tube for 10 min
  2. customthe pressure tube was sealed
  3. temperatureThe mixture was cooled to 23° C.
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified by FCC (3-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d5312996feb6415890bd40e6c0c6fded
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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