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Triethylamine → [1,1-Dimethyl-2-(7-thiophen-2-yl-1H-indol-3-yl)-ethyl)-carbamic acid tert-butyl ester

HRID 8094
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HRID 8094 반응식
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:29])([CH3:28])[CH2:10][C:11]1[C:19]2[C:14](=[C:15](OS(C(F)(F)F)(=O)=O)[CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:37]1[CH:41]=[CH:40][CH:39]=[C:38]1B(O)O>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]([CH3:29])([CH3:28])[CH2:10][C:11]1[C:19]2[C:14](=[C:15]([C:38]3[S:37][CH:41]=[CH:40][CH:39]=3)[CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)([CH3:2])([CH3:4])[CH3:3]
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참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 27339602-Thiopheneboronic acidHCID 86595245trifluoro-methanesulfonic acid 3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl ester

생성물 1

HCID 69517193[1,1-Dimethyl-2-(7-thiophen-2-yl-1H-indol-3-yl)-ethyl)-carbamic acid tert-butyl ester수율 31.3%

시약·촉매·용매 4

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매
HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of trifluoro-methanesulfonic acid 3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl ester (437 mg, 1.00 mmol) in dimethylformamide (6 mL) is added triethylamine (0.18 mL, 1.30 mmol), tetrakis(triphenylphosphine)-palladium (46 mg, 0.0401 mmol) and 2-thiopheneboronic acid (167 mg, 1.30 mmol). The mixture is refluxed for 22 hours, then cooled and diluted with brine and ethyl acetate. The organic phase is washed 7 times with brine. The organics are dried over anhydrous sodium sulfate, filtered and then evaporated in vacuo. The residue is purified using silica gel chromatography (hexane/20%.ethyl acetate, hexane gradient elution) to give 116 mg of [1,1-Dimethyl-2-(7-thiophen-2-yl-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester (31%). FDMS m/e=371 (M++1).

후처리

  1. temperatureThe mixture is refluxed for 22 hours
  2. temperaturecooled
  3. washThe organic phase is washed 7 times with brine
  4. dry with materialThe organics are dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue is purified
  8. washsilica gel chromatography (hexane/20%.ethyl acetate, hexane gradient elution)

출처 및 근거

ORD 기록
ord-0732badd337946498b912644452a820b
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07087635B2

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