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Nitrogen → 4-[5-Amino-2-(2,4-difluorophenoxy)phenyl]-2-methyl-2,7-naphthyridin-1-one

HRID 575559
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HRID 575559 반응식
N#N.[F:3][C:4]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:5]=1[O:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][C:8]=1B1OC(C)(C)C(C)(C)O1.Br[C:29]1[C:38]2[C:33](=[CH:34][N:35]=[CH:36][CH:37]=2)[C:32](=[O:39])[N:31]([CH3:40])[CH:30]=1.C([O-])([O-])=O.[K+].[K+]>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]>[NH2:11][C:10]1[CH:12]=[CH:13][C:7]([O:6][C:5]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:4]=2[F:3])=[C:8]([C:29]2[C:38]3[C:33](=[CH:34][N:35]=[CH:36][CH:37]=3)[C:32](=[O:39])[N:31]([CH3:40])[CH:30]=2)[CH:9]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 896576134-(2,4-Difluorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 1180220834-Bromo-2-methyl-1,2-dihydro-2,7-naphthyridin-1-one

생성물 1

HCID 1180217274-[5-Amino-2-(2,4-difluorophenoxy)phenyl]-2-methyl-2,7-naphthyridin-1-one수율 53.1%

시약·촉매·용매 3

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

실험 절차

For 5 min, N2 was bubbled through a mixture of 4-(2,4-difluorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (64.8 mg, 0.187 mmol), the title compound of Example 51, step 2 (30.0 mg, 0.124 mmol), K2CO3 (51.6 mg, 0.374 mmol) and Pd(dppf)Cl2 (18.3 mg, 0.025 mmol) in dioxane (2.0 mL) and water (0.2 mL) which was then microwaved at 100° C. for 1 h. Purification by preparative TLC (DCM:MeOH=20:1, Rf=0.5) gave the title compound (25.0 mg, 53%) as yellow gum. LCMS: 380.0 (M+H)+

후처리

  1. customPurification by preparative TLC (DCM:MeOH=20:1, Rf=0.5)

출처 및 근거

ORD 기록
ord-2f7095a51b5b40728ed8c39bc8d2e76a
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09034900B2

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