Sodium Carbonate → (Z)-4-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2-oxo-1H-indol-4-yl]-benzoic acid methyl ester

HRID 382059

反応式

HRID 382059 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=[O:4].Br[C:15]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[C:20]2[C:16]=1/[C:17](=[CH:28]/[C:29]1[NH:30][CH:31]=[CH:32][C:33]=1[O:34][CH3:35])/[C:18](=[O:27])[NH:19]2.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][C:8]([C:15]2[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[C:20]3[C:16]=2/[C:17](=[CH:28]/[C:29]2[NH:30][CH:31]=[CH:32][C:33]=2[O:34][CH3:35])/[C:18](=[O:27])[NH:19]3)=[CH:7][CH:6]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 18359293(Z)-1,3-dihydro-4-bromo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one2 回

生成物 1

HCID 9823378(Z)-4-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2-oxo-1H-indol-4-yl]-benzoic acid methyl ester収率 71.4%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

Using Method S above, 4-methoxycarbonyl-phenyl boronic acid (29.6 mg, 0.164 mmol) (from Step A above) was coupled with (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one (50 mg, 0.137 mmol) (Starting Material 6) using DPPFPdCl2 (5.6 mg) (Aldrich) as catalyst in aqueous 2M Na2CO3 (0.14 mL, 0.28 mmol) and DME (5 mL) at reflux for 18 h to give (Z)-4-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2-oxo-1H-indol-4-yl]-benzoic acid methyl ester (yield: 41 mg, 71%).

後処理

  1. temperatureat reflux for 18 h

出典と根拠

ORDレコード
ord-79ab16caab0746f7bcd6c7470a897789
出典データセット
uspto-grants-2001_10
特許番号
US06307056B1

関連ノート

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