1,1'-Carbonyldiimidazole → methyl 4-bromo-2-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}benzoate

HRID 1182239

反応式

HRID 1182239 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([OH:16])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[Br:29][C:30]1[CH:31]=[C:32]([NH2:40])[C:33](=[CH:38][CH:39]=1)[C:34]([O:36][CH3:37])=[O:35].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.O1CCCC1>[Br:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[C:32]([NH:40][C:14](=[O:16])[CH2:13][C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=3)[NH:8][C:7]=2[CH3:12])[CH:31]=1

参加物

7

反応物 4

HCID 682631,1'-CarbonyldiimidazoleHCID 761515-Methoxy-2-methylindole-3-acetic acidHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 17871390Methyl 2-Amino-4-bromobenzoate

生成物 1

HCID 69354325methyl 4-bromo-2-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}benzoate収率 66.6%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

5-Methoxy-2-methyl-3-indole acetic acid (5 g, obtainable from Acros), carbonyidiimidazole (4.44 g) and tetrahydrofuran (120 ml) were stirred at room temperature for 30 min after which methyl 4-bromoanthranilate (5.24 g) and pyridinium tosylate (13.69 g) were added and the mixture refluxed for 14 h. After diluting with dichloromethane (200 ml), the residue was washed with 2M hydrochloric acid (200 ml), 2M sodium hydroxide (200 ml), water (200 ml) and brine (200 ml) and dried (MgSO4). After solidifying by treatment with cyclohexane and ethyl acetate, the solid was triturated with ether to afford methyl 4-bromo-2-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}benzoate (6.54 g), MH+ 433, 435; MH− 431, 433; TR 3.67 min.

後処理

  1. additionwere added
  2. temperaturethe mixture refluxed for 14 h
  3. washthe residue was washed with 2M hydrochloric acid (200 ml), 2M sodium hydroxide (200 ml), water (200 ml) and brine (200 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solid was triturated with ether

出典と根拠

ORDレコード
ord-b71ed51311ea431bae8aa2e80406c250
出典データセット
uspto-grants-2007_10
特許番号
US07288564B2

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