Dichloromethane → 1-Cyano-7-(2-fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

HRID 1481010ノート

反応式

HRID 1481010 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](I)[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])[CH:9]=2)=[O:4].[C:25]([Cu])#[N:26].C(Cl)Cl>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:25]#[N:26])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])[CH:9]=2)=[O:4]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 898130397-(2-Fluoro-phenoxy)-4-hydroxy-1-iodo-isoquinoline-3-carboxylic acid methyl esterHCID 178418546HCID 178418546、化合物

生成物 1

HCID 898129021-Cyano-7-(2-fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

7-(2-Fluoro-phenoxy)-4-hydroxy-1-iodo-isoquinoline-3-carboxylic acid methyl ester (100 mg, 0.23 mmol) and CuCN (41 mg, 0.46 mmol) were suspended in DMF (1.0 mL). The resulting mixture was heated at 120° C. for 7 minutes and then cooled to room temperature. The reaction crude was poured into CH2Cl2 (30 mL) and stirred vigorously for 10 minutes at room temperature. The resulting suspension was filtered through a pad of celite and the filtrate was washed with H2O and brine sequentially. The organic layer was dried over MgSO4, concentrated, and purified by flash chromatography (0-50% EtOAc/hexanes) to give the title compound in 75 mg. 1H NMR (CDCl3, 200 MHz): δ=12.27 (s, 1H), 8.45 (d, 1H, J=9.0 Hz), 7.63-7.57 (m, 1H), 7.50-7.48 (m, 1H), 7.29-7.20 (m, 4H), 4.11 (s, 3H).

後処理

  1. temperaturecooled to room temperature
  2. customThe reaction crude
  3. filtrationThe resulting suspension was filtered through a pad of celite
  4. washthe filtrate was washed with H2O and brine sequentially
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. custompurified by flash chromatography (0-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-0ad623ff86fb4f6a94c5cc5aacfaf0d1
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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