Sodium Carbonate → 6-Phenyl-8-(3-nitrophenyl)-1,7-naphthyridine

HRID 369029

Reaction equation

HRID 369029 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[N:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)(=O)=O.[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C.[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:28]1([C:7]2[CH:8]=[C:9]3[C:14](=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=4)[N:16]=2)[N:13]=[CH:12][CH:11]=[CH:10]3)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 108109346-Trifluoromethylsulfonyloxy-8-(3-nitrophenyl)-1,7-naphthyridine

Product 1

HCID 107112816-Phenyl-8-(3-nitrophenyl)-1,7-naphthyridine

Reagents, catalysts & solvents 3

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-trifluoromethylsulfonyloxy-8-(3-nitrophenyl)-1,7-naphthyridine (300 mg, 0.75 mmol; prepared according to example 8) in tetrahydrofuran (5 ml) is added phenylboronic acid (118 mg, 0.97 mmol, bis(dibenzylideneacetone) palladium (18 mg, 0.03 mmol), triphenylphosphine (16 mg, 0.06 mmol) and aqueous Na2CO3 (2N, 1.44 ml). The solution is kept at 60° C. for 20 h. The solution is diluted with ethyl acetate, filtered and washed with 1N NaOH and water. The solvent is removed in vacuo to give pure product. Mass M+H 328. mp 172-175° C.

Workup

  1. filtrationfiltered
  2. washwashed with 1N NaOH and water
  3. customThe solvent is removed in vacuo
  4. customto give pure product

Sources & evidence

ORD record
ord-7cb50492b9bc48328debc03e0aaab1ab
Source dataset
uspto-grants-2000_10
Patent number
US06136821

Linked notes

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