홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Nitrogen → 4-Allyl-5-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine

HRID 1400720
노트
인쇄 미리보기

반응식

HRID 1400720 반응식
[Cl:1][C:2]1[C:11]2[NH:10][CH2:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[B:12]1[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]1.C([O-])([O-])=O.[K+].[K+].N#N.[CH2:29](Br)[CH:30]=[CH2:31]>CN(C=O)C.O>[CH2:31]([N:10]1[CH2:9][CH2:8][O:7][C:6]2[CH:5]=[CH:4][C:3]([B:12]3[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]3)=[C:2]([Cl:1])[C:11]1=2)[CH:30]=[CH2:29]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 947NitrogenHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 595786245-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine

생성물 1

HCID 867107714-Allyl-5-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine수율 84.2%

시약·촉매·용매 2

HCID 962Water용매
HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

A solution of 5-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (0.504 g, 1.426 mmol, Ref. WO20100130034) and K2CO3 (0.504 g, 3.65 mmol) in dry DMF (5 mL) was sparged with N2 for 5 min, then treated with allyl bromide (0.8 mL, 9.17 mmol). The reaction tube was sealed and then heated (70° C.) for 22 h, then cooled and diluted with water (50 mL) and extracted into EtOAc (50 mL). The organic layer was washed with water, brine, then dried (Na2SO4), filtered, concentrated, and purified by biotage chromatography (4 g SiO2, 0% (3 CV), 0-40% (15 CV), 40% (2 CV); EtOAc in hexanes) to afford the desired product (0.403 g, 1.201 mmol, 84% yield) as a clear viscous oil. 1H NMR (500 MHz, CDCl3) δ 7.30 (d, J=8.2 Hz, 1H), 6.79 (d, J=8.2 Hz, 1H), 6.15-6.02 (m, 1H), 5.31 (dd, J=17.2, 1.4 Hz, 1H), 5.28-5.21 (m, 1H), 4.18-4.13 (m, 2H), 3.59 (d, J=6.0 Hz, 2H), 3.14-3.07 (m, 2H), 1.36 (s, 12H). LCMS (M+H)=336.9.

후처리

  1. customThe reaction tube was sealed
  2. temperaturecooled
  3. extractionextracted into EtOAc (50 mL)
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by biotage chromatography (4 g SiO2, 0% (3 CV), 0-40% (15 CV), 40% (2 CV); EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-4dc07a664aea4b5cacfab6ff8c2665d0
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08906929B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트