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

HRID 369029

반응식

HRID 369029 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladium촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-7cb50492b9bc48328debc03e0aaab1ab
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06136821

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