Hydrochloric Acid → HCID 136377240、化合物

HRID 919913ノート

反応式

HRID 919913 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:24])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9](Br)=[CH:8]2)=[O:4].[N:25]1[O:29][N:28]=[C:27]2[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][C:26]=12.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.Cl>C1(C)C=CC=CC=1.[Cl-].[Na+].O.CC([O-])=O.CC([O-])=O.[Pd+2].CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:24])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9]([C:31]1[CH:32]=[CH:33][C:26]3[C:27]([CH:30]=1)=[N:28][O:29][N:25]=3)=[CH:8]2)=[O:4]

参加物

11

反応物 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 4672597Benzo[C][1,2,5]Oxadiazole-5-Boronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 682974771-Benzyl-3-bromo-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

生成物 1

HCID 136377240HCID 136377240、化合物収率 36.7%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1-benzyl-3-bromo-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (80 mg, 0.21 mmol), benzo[1,2,5]oxadiazole-5-boronic acid (51 mg, 0.31 mmol), K3PO4 (87 mg, 0.41 mmol), H2O (7.4 mg, 0.41 mmol), SPhos (4.2 mg, 0.010 mmol) and Pd(OAc)2 (4.2 mg, 0.0062 mmol) in toluene (5 mL) was heated at 100° C. under nitrogen atmosphere for 16 h. After the mixture was cooled to r.t., brine and EtOAc were added. 1 M HCl was added with stirring until pH was about 3, and the organic layer was dried over MgSO4 and concentrated. The crude product was first purified by silica gel chromatography (0-60% EtOAc/hexanes+1% AcOH), then by preparative TLC (20% EtOAc/CH2Cl2) to give 33 mg of the title compound. MS: (+) m/z 429.27 (M+1).

後処理

  1. temperatureAfter the mixture was cooled to r.t.
  2. dry with materialthe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was first purified by silica gel chromatography (0-60% EtOAc/hexanes+1% AcOH)

出典と根拠

ORDレコード
ord-b8ab95a9b5004163b191976db4a9fab9
出典データセット
uspto-grants-2016_03
特許番号
US09271970B2

反応ノート

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