Triethylamine → 2-(4-bromo-2-fluorophenyl)-N-(2,5-difluorophenyl)acetamide

HRID 1428631노트

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HRID 1428631 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[C:4]([F:12])[CH:3]=1.[F:13][C:14]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:15]=1[NH2:16].CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:16][C:15]2[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:14]=2[F:13])=[O:11])=[C:4]([F:12])[CH:3]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 677752,5-DifluoroanilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 140537922-(4-Bromo-2-fluorophenyl)acetic acid

생성물 1

HCID 904159652-(4-bromo-2-fluorophenyl)-N-(2,5-difluorophenyl)acetamide수율 35.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
20 °C

실험 절차

To a solution of 2-(4-bromo-2-fluorophenyl)acetic acid (180 mg, 0.775 mmol) and 2,5-difluoroaniline (100 mg, 0.775 mmol) in DCM (20 mL) was added Et3N (0.324 mL, 2.324 mmol) and HATU (884 mg, 2.324 mmol) in portions. Then the mixture was stirred at 20° C. for 3 h. After LCMS analysis showed the starting material had disappeared, the solvent was removed in vacuo. Then the crude product was dissolved in DCM and washed with H2O and brine. The organic layer was evaporated to dryness. The crude product which was purified by silica column chromatography (PE/EA 100/1 to 10/1) to afford 2-(4-bromo-2-fluorophenyl)-N-(2,5-difluorophenyl)acetamide (103 mg, 0.276 mmol, 35.6% yield). 1H NMR: (400 MHz, CD3OD) δ 7.87-7.82 (m, 1H), 7.39-7.26 (m, 3H), 7.20-7.13 (m, 1H), 6.90-6.82 (m, 1H), 3.83 (s, 2H); ES-LCMS: m/z 343.9 (M+H).

후처리

  1. customthe solvent was removed in vacuo
  2. dissolutionThen the crude product was dissolved in DCM
  3. washwashed with H2O and brine
  4. customThe organic layer was evaporated to dryness
  5. customThe crude product which was purified by silica column chromatography (PE/EA 100/1 to 10/1)

출처 및 근거

ORD 기록
ord-c12a2c0af4924693a3214f998658f282
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937071B2

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