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

HRID 369029

反応式

HRID 369029 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladium触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-7cb50492b9bc48328debc03e0aaab1ab
出典データセット
uspto-grants-2000_10
特許番号
US06136821

関連ノート

読み込み中…