1-Bromo-4-fluorobenzene → HCID 59283079, compound

HRID 1965848Notes

Reaction equation

HRID 1965848 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1.CC1(C)C(C)(C)OB([C:21]2[S:22][C:23](B3OC(C)(C)C(C)(C)O3)=[CH:24][CH:25]=2)O1.Br[C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=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.O1CCOCC1>[F:43][C:40]1[CH:41]=[CH:42][C:37]([C:23]2[S:22][C:21]([C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=3)=[CH:25][CH:24]=2)=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 99931-Bromo-4-fluorobenzeneHCID 10340Sodium CarbonateHCID 27950292-Chloro-6-methoxy-3-nitropyridineHCID 230580612,2'-(Thiene-2,5-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Product 1

HCID 59283079HCID 59283079, compoundYield 12.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 2-chloro-6-methoxy-3-nitropyridine (94 mg, 0.5 mmol), 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene (168 mg, 0.5 mmol), 1-bromo-4-fluorobenzene (105 mg, 0.6 mmol), 1.5 mL of dioxane, 1.5 mL of 1 M Na2CO3, and tetrakis(triphenylphosphine)palladium (29 mg, 0.025 mmol) was heated in a microwave reactor at 95 C for 10 min. It was concentrated under reduced pressure and the residue was chromatographed (EtOAc/hexane) to afford 2-(5-(4-fluorophenyl)thiophen-2-yl)-6-methoxy-3-nitropyridine (WZ02103) as a yellow solid (20 mg, 12%). MS (ESI) m/z 330 (M+H+).

Workup

  1. temperaturewas heated in a microwave reactor at 95 C for 10 min
  2. concentrationIt was concentrated under reduced pressure
  3. customthe residue was chromatographed (EtOAc/hexane)

Sources & evidence

ORD record
ord-152ff8e465534e0c8b2c4531ca52613b
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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