Hydrochloric Acid → HCID 89812805、化合物

HRID 1481153ノート

反応式

HRID 1481153 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10](Br)[CH:9]=2)=[O:4].C([Sn](CCCC)(CCCC)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)CCC.CCOC(C)=O.Cl>CN(C=O)C.[Cl-].[Na+].O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:9]=2)=[O:4]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 607632TributylphenyltinHCID 89813103Methyl 7-bromo-4-hydroxyisoquinoline-3-carboxylate

生成物 1

HCID 89812805HCID 89812805、化合物収率 75.6%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
120 °C

実験手順

A mixture of 7-bromo-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (400 mg, 1.42 mmol), tributylphenyltin (0.6 mL, 1.70 mmol), and PdCl2(PPh3)2 (200 mg, 0.28 mmol) in DMF (14 mL) was heated at 120° C. for 2 h under N2 atmosphere. After cooling the mixture to r.t., brine (10 mL) and EtOAc (30 mL) were added. 1 M HCl was added with stirring until pH was ˜3. The aqueous layer was extracted with additional EtOAc, and the organic layers were combined, washed with water, and dried over MgSO4. After evaporating the solvent, the crude product was purified by column chromatography (0-40% EtOAc/hexanes) to give 300 mg of the title compound. 1H NMR (CDCl3, 200 MHz): δ ppm=11.7 (s, 1H), 8.87 (s, 1H), 8.46 (d, 1H, J=8.6 Hz), 8.15 (d, 1H, J=1.4 Hz), 8.04 (dd, 1H, J=8.6 Hz, 2.0 Hz), 7.65-7.80 (m, 2H), 7.40-7.60 (m, 3H), 4.12 (s, 3H).

後処理

  1. temperatureAfter cooling the mixture to r.t.
  2. extractionThe aqueous layer was extracted with additional EtOAc
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customAfter evaporating the solvent
  6. customthe crude product was purified by column chromatography (0-40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-108816d123b24f489d36597439284049
出典データセット
uspto-grants-2016_08
特許番号
US09409892B2

反応ノート

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