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Nitrogen → 5-[5-Amino-2-(2,4-difluorophenoxyl)phenyl]-7-methylimidazo[1,5-a]pyrazin-8-one

HRID 518347
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HRID 518347 반응식
Br[C:2]1[N:7]2[CH:8]=[N:9][CH:10]=[C:6]2[C:5](=[O:11])[N:4]([CH3:12])[CH:3]=1.[F:13][C:14]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:15]=1[O:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][C:18]=1B1OC(C)(C)C(C)(C)O1.C([O-])(O)=O.[Na+].N#N>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:21][C:20]1[CH:22]=[CH:23][C:17]([O:16][C:15]2[CH:33]=[CH:34][C:35]([F:37])=[CH:36][C:14]=2[F:13])=[C:18]([C:2]2[N:7]3[CH:8]=[N:9][CH:10]=[C:6]3[C:5](=[O:11])[N:4]([CH3:12])[CH:3]=2)[CH:19]=1
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참가 물질

8

반응물 4

HCID 947NitrogenHCID 516892Sodium BicarbonateHCID 896576134-(2,4-Difluorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 1180225995-Bromo-7-methylimidazo[1,5-a]pyrazin-8(7h)-one

생성물 1

HCID 1180221575-[5-Amino-2-(2,4-difluorophenoxyl)phenyl]-7-methylimidazo[1,5-a]pyrazin-8-one수율 60%

시약·촉매·용매 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A solution of 5-bromo-7-methylimidazo[1,5-a]pyrazin-8-one (114.0 mg, 0.5 mmol), the title compound of Example 57, step 1 (208.0 mg, 0.6 mmol), Pd(dppf)2Cl2 (37.0 mg, 0.05 mmol), NaHCO3 (126.0 mg, 1.5 mmol) in dioxane (10 mL) and H2O (1 mL) was stirred in microwave at 110° C. with N2 atmosphere for 3 hours. The solvent was evaporated to give the crude product, which was purified by column chromatography (PE:EA=3/1) to give the title compound (110 mg, 60%) as a yellow solid. 1H NMR (CDCl3 400 MHz) δ 7.94 (s, 1H), 7.82 (s, 1H), 6.93-6.82 (m, 2H), 6.79-6.74 (m, 4H), 6.41 (s, 1H), 3.50 (s, 3H). LCMS (M+H)+ 369.

후처리

  1. customThe solvent was evaporated
  2. customto give the crude product, which
  3. customwas purified by column chromatography (PE:EA=3/1)

출처 및 근거

ORD 기록
ord-4a65bdb7cb5e4ec2ae96bc0d5e763f03
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115114B2

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