Diisopropylethylamine → N-(4-bromobenzyl)-2-nitro-4-(quinolin-2-ylmethoxy)aniline

HRID 2178424노트

반응식

HRID 2178424 반응식
F[C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].Cl.[Br:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[Br:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:2]2[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]3[CH:17]=[CH:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:9]=3)=[CH:4][C:3]=2[N+:20]([O-:22])=[O:21])=[CH:27][CH:26]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27240964-Bromobenzylamine hydrochlorideHCID 904169762-((4-Fluoro-3-nitrophenoxy)methyl)quinoline

생성물 1

HCID 90414040N-(4-bromobenzyl)-2-nitro-4-(quinolin-2-ylmethoxy)aniline수율 113.1%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
100 °C

실험 절차

To a 250 mL round-bottomed flask were added a stir bar, 2-((4-fluoro-3-nitrophenoxy)methyl)quinoline (15.0 g, 40 mmol) and 4-bromobenzyl amine hydrochloride (11 g, 50 mmol), DMA (130 mL), and DIPEA (22 mL, 125 mmol). The resulting mixture was heated to 100° C. After 24 h, the mixture was cooled and concentrated to dryness. The residue was triturated with IPA (200 mL) and the orange solid was collected by vacuum filtration. The collected solid was washed with IPA (2×50 mL) and hexanes (2×50 mL) to afford the title compound (21 g, 84%). MS (ESI): mass calcd. for C23H18BrN3O3, 463.05; m/z found 464.1 [M+H]+. 1H NMR (600 MHz, CDCl3) δ 8.34-8.27 (m, 1H), 8.21 (d, J=8.4, 1H), 8.12-8.06 (m, 1H), 7.87-7.81 (m, 2H), 7.75 (ddd, J=8.4, 6.9, 1.4, 1H), 7.63 (d, J=8.5, 1H), 7.58-7.53 (m, 1H), 7.49-7.46 (m, 2H), 7.25-7.18 (m, 3H), 6.71 (d, J=9.4, 1H), 5.34 (s, 2H), 4.49 (d, J=5.8, 2H).

후처리

  1. additionTo a 250 mL round-bottomed flask were added a stir bar
  2. temperaturethe mixture was cooled
  3. concentrationconcentrated to dryness
  4. customThe residue was triturated with IPA (200 mL)
  5. filtrationthe orange solid was collected by vacuum filtration
  6. washThe collected solid was washed with IPA (2×50 mL) and hexanes (2×50 mL)

출처 및 근거

ORD 기록
ord-0a0f55cd9ee34d0abe13cc3aff3b34d6
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067917B2

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