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

HRID 966534
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HRID 966534 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228
Dimethylformamide
용매

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온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a66721ec5b0d4e5bbbe1a4f65f94328c
출처 데이터셋
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06951848B2

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