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

Potassium Carbonate → N-Cyclopropyl-4-[8-(methylsulfanyl)-6-phenylimidazo[1,2-a]pyrazin-3-yl]benzamide

HRID 925593
노트
인쇄 미리보기

반응식

HRID 925593 반응식
Br[C:2]1[N:3]=[C:4]([S:23][CH3:24])[C:5]2[N:6]([C:8]([C:11]3[CH:22]=[CH:21][C:14]([C:15]([NH:17][CH:18]4[CH2:20][CH2:19]4)=[O:16])=[CH:13][CH:12]=3)=[CH:9][N:10]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(O)CC.CN1C(=O)CCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:18]1([NH:17][C:15](=[O:16])[C:14]2[CH:21]=[CH:22][C:11]([C:8]3[N:6]4[CH:7]=[C:2]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[N:3]=[C:4]([S:23][CH3:24])[C:5]4=[N:10][CH:9]=3)=[CH:12][CH:13]=2)[CH2:20][CH2:19]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 533898994-[6-Bromo-8-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylbenzamide

생성물 1

HCID 53389900N-Cyclopropyl-4-[8-(methylsulfanyl)-6-phenylimidazo[1,2-a]pyrazin-3-yl]benzamide수율 80.5%

시약·촉매·용매 4

HCID 11776Triphenylphosphine
촉매
HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매
HCID 10311-Propanol용매
HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

To a stirred solution of 4-(6-bromo-8-methylsulfanyl-imidazo[1,2-a]pyrazin-3-yl)-N-cyclopropyl-benzamide (7.34 g, 18.2 mmol) in n-propanol (270 mL) and NMP (15 mL) was subsequently added 27.3 mL 2M potassium carbonate solution, 4.44 g phenylboronic acid (36.4 mmol, 2 eq), triphenylphosphine (238.7 mg, 0.91 mmol, 0.05 eq), 1.28 g bis(triphenylphosphin)palladium(II)chloride (1.82 mmol, 0.1 eq) in one portion at rt under argon atmosphere. After stirring for 2 h at 120° C., the mixture was concentrated in vaccuo (50% v/v), triturated with water and extracted with DCM. The organic phase was dried over sodium sulphate, filtered and the solvent was evaporated. Purification by flash chromatography (ethyl acetate/n-hexane) followed by crystallization from ethyl acetate yielded 5.87 g (80.5%)N-Cyclopropyl-4-(8-methylsulfanyl-6-phenyl-imidazo[1,2-a]pyrazin-3-yl)-benzamide: 1H-NMR (300 MHz, CDCl3): δ=8.30 (1H, s), 7.94 (4H, d), 7.77 (1H, s), 7.65 (2H, d), 7.50-7.37 (3H, m), 6.38 (1H, bs), 2.95 (1H, m), 2.80 (3H, s), 1.04 (6H, d), 0.92 (2H, m), 0.67 (2H, m) ppm.

후처리

  1. customat rt
  2. concentrationthe mixture was concentrated in vaccuo (50% v/v),
  3. customtriturated with water
  4. extractionextracted with DCM
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customPurification by flash chromatography (ethyl acetate/n-hexane)
  9. customfollowed by crystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-a6e9224dd2f3497a83a0a649e4064504
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09284317B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트