Tolylboronic acid → Methyl 4-(benzyloxycarbonylamino)-5-bromo-2-p-tolylthiophene-3-carboxylate

HRID 1918216노트

반응식

HRID 1918216 반응식
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:19]([O:21][CH3:22])=[O:20])=[C:14](Br)[S:15][C:16]=1[Br:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(O)(O)[C:24]1[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=1>C(O)C.O.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:19]([O:21][CH3:22])=[O:20])=[C:14]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[S:15][C:16]=1[Br:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 79799Tolylboronic acidHCID 58191482Methyl 4-(((benzyloxy)carbonyl)amino)-2,5-dibromothiophene-3-carboxylate

생성물 1

HCID 58191383Methyl 4-(benzyloxycarbonylamino)-5-bromo-2-p-tolylthiophene-3-carboxylate

시약·촉매·용매 2

HCID 10340Sodium Carbonate용매HCID 86587398Ethanol toluene water용매

반응 조건

온도
80 °C

실험 절차

Palladium tetrakis-triphenylphosphine is added to a degassed solution of dibromide 155 and p-tolylboronic acid 175 in ethanol: water:toluene (2:1:1) and sodium carbonate. The resulting mixture is heated under N2 and stirred for 1 h at 80° C. The mixture is then cooled filtered through a 0.45 μm syringe filter and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provides 176.

후처리

  1. temperatureThe resulting mixture is heated under N2
  2. temperatureThe mixture is then cooled
  3. filtrationfiltered through a 0.45 μm syringe
  4. filtrationfilter
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c1ea89d8a4af4adb96c2cc940bf2214a
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618307B2

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