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

Sodium Carbonate → tert-butyl 6-cyclohexyl-5-(2-formyl-4-methoxyphenyl)-4-(2-methoxy-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1008967
노트
인쇄 미리보기

반응식

HRID 1008967 반응식
Br[C:2]1[N:6]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:5]2[CH:12]=[C:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[S:14][C:4]=2[C:3]=1[CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[CH:28]([C:30]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:31]=1B(O)O)=[O:29].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:22]1([C:3]2[C:4]3[S:14][C:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:12][C:5]=3[N:6]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:2]=2[C:31]2[CH:32]=[CH:33][C:34]([O:36][CH3:37])=[CH:35][C:30]=2[CH:28]=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 27343652-Formyl-4-methoxybenzeneboronic acidHCID 67298890tert-butyl 5-bromo-6-cyclohexyl-4-(2-methoxy-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

생성물 1

HCID 86629779tert-butyl 6-cyclohexyl-5-(2-formyl-4-methoxyphenyl)-4-(2-methoxy-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate수율 57%

시약·촉매·용매 3

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

실험 절차

tert-Butyl 5-bromo-6-cyclohexyl-4-(2-methoxy-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate (1 eq., prepared as described in Example 1, Step 3) and 2-formyl-4-methoxyphenylboronic acid (1.5 eq.) were dissolved in dioxane (0.1 M) and treated with 2 M Na2CO3 solution (2 eq.). The solution was degassed by bubbling argon through it and Pd(PPh3)2Cl2 (0.1 eq.) was added. The reaction mixture was heated to reflux for 20 min. After cooling down to RT, the mixture was diluted with EtOAc and washed with 1 N hydrochloric acid and with brine. The organic layer was dried over sodium sulfate and evaporated in vacuo and the residue purified by chromatography (PE:EtOAc, 9:1) to afford the pure title compound (57%) as a solid. 1H-NMR (400 MHz, DMSO-d6, 300 K, δ) 9.64 (s, 1H), 7.89 (s, 1H), 7.43 (s, 1H), 7.41-7.38 (m, 2H), 4.92 (d, J 18.0, 1H), 4.73 (d, J 18.0, 1H), 3.90 (s, 3H), 3.50 (s, 3H), 2.14-2.09 (m, 1H), 1.73-1.19 (m, 10H), 1.54 (s, 9H). MS (ES+) m/z: 534 [M+Na]+.

후처리

  1. customThe solution was degassed
  2. additionwas added
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 20 min
  5. washwashed with 1 N hydrochloric acid and with brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customevaporated in vacuo
  8. customthe residue purified by chromatography (PE:EtOAc, 9:1)

출처 및 근거

ORD 기록
ord-cb61a01262384ae982e879b7232d75ed
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07973026B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트