Ethanol → (2-Chlorophenyl)-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)thiophene-2-carboxamide

HRID 1951255

반응식

HRID 1951255 반응식
Br[C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[CH:15]=[C:14]([C:16](=[O:21])[NH:17][CH:18]3[CH2:20][CH2:19]3)[CH:13]=[CH:12][C:11]=2[CH3:22])=[O:8])=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.C(O)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:4]1[CH:3]=[CH:2][S:6][C:5]=1[C:7]([NH:9][C:10]1[CH:15]=[C:14]([C:16](=[O:21])[NH:17][CH:18]2[CH2:20][CH2:19]2)[CH:13]=[CH:12][C:11]=1[CH3:22])=[O:8]

참가 물질

8

반응물 4

HCID 702EthanolHCID 62657Potassium Phosphate, TribasicHCID 27343222-Chlorophenylboronic acidHCID 597614015-Bromo-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)thiophene-2-carboxamide

생성물 1

HCID 67148792(2-Chlorophenyl)-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)thiophene-2-carboxamide수율 64.9%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
115 °C

실험 절차

5-Bromo-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)thiophene-2-carboxamide (80 mg, 0.21 mmol) and 2-chlorophenylboronic acid (50 mg, 0.32 mmol) in toluene (0.7 mL) was purged with argon and ethanol (0.14 mL), 2 M aq. K3PO4 (0.21 mL, 0.42 mmol), and Pd(PPh3)4 (12 mg, 0.010 mmol) was added. The resulting mixture was heated at 115° C. for 2 h. After cooling to rt, the mixture was diluted with EtOAc (100 mL), washed with brine and dried over anyhd. sodium sulfate. The solution was filtered and concentrated under vacuum to afford a yellow solid which was triturated with MeOH (2 mL), filtered to collect the solid and rinsed with additional MeOH (2×0.5 mL) and dried under vacuum to afford 56 mg of a white solid as the title compound (Example 136). HPLC Ret time=3.56 min. LCMS [M+H]+ 411.21.

후처리

  1. additionwas added
  2. temperatureAfter cooling to rt
  3. washwashed with brine
  4. customdried over anyhd
  5. filtrationThe solution was filtered
  6. concentrationconcentrated under vacuum
  7. customto afford a yellow solid which
  8. customwas triturated with MeOH (2 mL)
  9. filtrationfiltered
  10. customto collect the solid
  11. washrinsed with additional MeOH (2×0.5 mL)
  12. customdried under vacuum

출처 및 근거

ORD 기록
ord-421b4ee044604b31a6989cd9d90770f8
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404689B2

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