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Tripropylamine → 5-(tert-Butoxycarbonylamino-methyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966534
ノート
印刷プレビュー

反応式

HRID 966534 の反応式
[CH2:1]([O:8][C:9](=[O:30])/[CH:10]=[C:11](/[NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:16][C:15]=1I)\[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CCC)CCC)CC>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:18]=2)[NH:13][C:11]=1[CH3:12])=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 7616TripropylamineHCID 23393855(E)-3-[4-(tert-Butoxycarbonylamino-methyl)-2-iodo-phenylamino]-but-2-enoic Acid Benzyl Ester

生成物 1

HCID 102940355-(tert-Butoxycarbonylamino-methyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester収率 48.2%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228
Dimethylformamide
溶媒

反応条件

温度
120 °C

実験手順

To a mixture of (E)-3-[4-(tert-butoxycarbonylamino-methyl)-2-iodo-phenylamino]-but-2-enoic acid benzyl ester (5.25 g, 10 mmol) and tripropylamine (1.9 mL, 10 mmol) in DMF (10 mL) was added palladium acetate (112 mg, 0.5 mmol). The mixture was stirred at 120° C. for 1 hour and then partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give a residue, which was recrystallized from ethyl acetate and hexanes to give 1.9 g (48%) of the desired product as a yellowish solid: MS(APCI−): m/z 393.1.4 (M−H).

後処理

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give a residue, which
  7. customwas recrystallized from ethyl acetate and hexanes

出典と根拠

ORDレコード
ord-a66721ec5b0d4e5bbbe1a4f65f94328c
出典データセット
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06951848B2

反応ノート

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