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

HRID 1776717노트

반응식

HRID 1776717 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-a57bf5f0675241dc834cdeb7123bff69
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265770B2

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