Sodium Carbonate → 6-(4-Carboxyphenyl)-8-methoxy-1,7-naphthyridine

HRID 369035

반응식

HRID 369035 반응식
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([O:17][CH3:18])[N:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)(=O)=O.[C:21]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)([OH:23])=[O:22].C([O-])([O-])=O.[Na+].[Na+]>CN(C=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.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[C:21]([C:24]1[CH:29]=[CH:28][C:27]([C:7]2[CH:8]=[C:9]3[C:14](=[C:15]([O:17][CH3:18])[N:16]=2)[N:13]=[CH:12][CH:11]=[CH:10]3)=[CH:26][CH:25]=1)([OH:23])=[O:22]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 232846356-Trifluoromethylsulfonyloxy-8-methoxy-1,7-naphthyridine

생성물 1

HCID 232846426-(4-Carboxyphenyl)-8-methoxy-1,7-naphthyridine수율 80.8%

시약·촉매·용매 3

HCID 80271Tri-o-tolylphosphine촉매HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladium촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 6-trifluoromethylsulfonyloxy-8-methoxy-1,7-napthyridine (1.5 g, 4.86 mmol) in DMF (40 ml) is added 4-carboxy-phenylboronic acid (0.866 g, 5.34 mmol), bis(dibenzylidenacetone) palladium (112 mg, 0.167 mmol), tri-o-tolylphosphine (96 mg, 0.32 mmol) and aqueous Na2CO3 (14.6 ml, 2N,). The reaction mixture is stirred at 110° for 3 h. The hot solution is filtred through cellit and the solution evaporated to dryness. The crude product is dissolved in hot water (60 ml) and the water phase washed with ethyl acetate (3×50 ml). The product is precipitated from the water phase by carefully adding aqueous HCl (2N, 6 ml). The suspension is filtered and the crude product is stirred again in hot ethyl acetate (50 ml). The cold suspension is filtered to yield the title compound (1.10 g). M+280; Melting point >300°.

후처리

  1. customthe solution evaporated to dryness
  2. dissolutionThe crude product is dissolved in hot water (60 ml)
  3. washthe water phase washed with ethyl acetate (3×50 ml)
  4. customThe product is precipitated from the water phase by carefully adding aqueous HCl (2N, 6 ml)
  5. filtrationThe suspension is filtered
  6. stirringthe crude product is stirred again in hot ethyl acetate (50 ml)
  7. filtrationThe cold suspension is filtered

출처 및 근거

ORD 기록
ord-449fc1ba55304cbb90163e63a52ba620
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06136821

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