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

HRID 1182239

반응식

HRID 1182239 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b71ed51311ea431bae8aa2e80406c250
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288564B2

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