N-Ethyl-1-naphthalenamine → Ethyl 7-bromo-3-(3-(ethyl(naphthalen-1-yl)amino)propyl)-1h-indole-2-carboxylate

HRID 576280

反応式

HRID 576280 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH:18]=O.[CH2:20]([NH:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)[CH3:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][N:22]([CH2:20][CH3:21])[C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

参加物

6

反応物 3

HCID 67043N-Ethyl-1-naphthalenamineHCID 5049666Sodium triacetoxyborohydrideHCID 86628021ethyl 7-bromo-3-(3-oxopropyl)-1H-indole-2-carboxylate

生成物 1

HCID 68938635Ethyl 7-bromo-3-(3-(ethyl(naphthalen-1-yl)amino)propyl)-1h-indole-2-carboxylate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of EXAMPLE 531A (130 mg) and N-ethylnaphthalen-1-amine (82 mg) in dichloromethane (3 mL) was added sodium triacetoxyborohydride (2.35 g). The mixture was stirred at room temperature overnight. After this time the mixture was diluted with ethyl acetate (1500 mL) and washed with 1N NaOH, water, brine, and dried over Na2SO4. After filtration and concentration of the filtrate, the residue was purified by flash chromatography using silica gel and eluenting with 5% ethyl acetate in hexane.

後処理

  1. washwashed with 1N NaOH, water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and concentration of the filtrate
  4. customthe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-6cd87c6596114d6ba0b4f35bd098973b
出典データセット
uspto-grants-2015_05
特許番号
US09035047B2

関連ノート

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