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

Diisopropylethylamine → 4-(5-[(4-Fluorophenyl)methyl]-6-methylpyrimidin-4-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine

HRID 241170
노트
인쇄 미리보기

반응식

HRID 241170 반응식
FC(F)(F)C(O)=O.[CH3:8][C:9]1([CH3:27])[C:13]([CH3:15])([CH3:14])[O:12][B:11]([C:16]2[CH:17]=[CH:18][C:19]3[O:25][CH2:24][CH2:23][N:22]=[CH:21][C:20]=3[CH:26]=2)[O:10]1.Cl[C:29]1[C:34]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)=[C:33]([CH3:43])[N:32]=[CH:31][N:30]=1.C(N(CC)C(C)C)(C)C>CN1CCCC1=O>[F:42][C:39]1[CH:38]=[CH:37][C:36]([CH2:35][C:34]2[C:29]([N:22]3[CH2:21][C:20]4[CH:26]=[C:16]([B:11]5[O:10][C:9]([CH3:27])([CH3:8])[C:13]([CH3:14])([CH3:15])[O:12]5)[CH:17]=[CH:18][C:19]=4[O:25][CH2:24][CH2:23]3)=[N:30][CH:31]=[N:32][C:33]=2[CH3:43])=[CH:41][CH:40]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 668206407-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazepine trifluoroacetate saltHCID 866478404-Chloro-5-(4-fluorobenzyl)-6-methylpyrimidine

생성물 1

HCID 668205164-(5-[(4-Fluorophenyl)methyl]-6-methylpyrimidin-4-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine수율 42%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A mixture of 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazepine trifluoroacetate salt (2.9 g, 8.00 mmol, 4-chloro-5-[(4-fluorophenyl)methyl]-6-methylpyrimidine (reagent preparation 5) (1.9 g, 8.00 mmol) and N,N-diisopropylethylamine (7.0 mL, 40.0 mmol) in N-methyl-2-pyrrolidone (10 mL) was reacted in a microwave apparatus (250 W) for 2 h at 150° C. After cooling to room temperature the reaction mixture was partitioned between ethyl acetate (500 mL) and brine (100 mL). The organic layer was separated, washed with brine (100 mL), dried over sodium sulfate then filtered and concentrated. Column chromatography of the residue on silica (gradient 20 to 40% ethyl acetate in hexane) gave 4-{5-[(4-fluorophenyl)methyl]-6-methylpyrimidin-4-yl}-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine (1.6 g, 42% yield). 1H NMR (400 MHz, DMSO-D6): 8.58 (s, 1H), 7.62 (dd, 1H), 7.08 (m, 4H), 7.02 (d, 1H), 6.96 (d, 1H), 4.36 (s, 2H), 4.30 (m, 2H), 3.92 (s, 2H), 3.84 (m, 2H), 2.26 (s, 3H), 1.36 (s, 12H); MS (EI) for C27H31BFN3O3: 476 (MH+).

후처리

  1. customwas reacted in a microwave apparatus (250 W) for 2 h at 150° C
  2. customwas partitioned between ethyl acetate (500 mL) and brine (100 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationthen filtered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-581438f99b2f4abf81c076b4e4397c62
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08648066B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트