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

HRID 369035

反応式

HRID 369035 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 80271Tri-o-tolylphosphine触媒HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladium触媒HCID 6228Dimethylformamide溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-449fc1ba55304cbb90163e63a52ba620
出典データセット
uspto-grants-2000_10
特許番号
US06136821

関連ノート

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