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Sodium Carbonate → HCID 71547691, 화합물

HRID 1771153
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HRID 1771153 반응식
C(=O)([O:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][C:21](Cl)=[N:20]3)=[O:16])[C:9]=1[F:28])OC(C)(C)C.[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])([O-])=O.[Na+].[Na+]>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]>[F:28][C:9]1[C:8]([OH:7])=[CH:13][CH:12]=[C:11]([F:14])[C:10]=1[C:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][C:21]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[N:20]2)=[O:16]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 89484872HCID 89484872, 화합물

생성물 1

HCID 71547691HCID 71547691, 화합물

시약·촉매·용매 3

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

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온도
100 °C

실험 절차

A mixture of tert-butyl (3-(3-chloroquinoxaline-6-carbonyl)-2,4-difluorophenyl) carbonate (60 mg, 0.14 mmol, 1.0 eq.), phenylboronic acid (17 mg, 0.14 mmol, 1.1 eq.), Pd(dppf)2Cl2 (6 mg, 0.007 mmol, 0.05 eq.) and Na2CO3 (30 mg, 0.28 mmol, 2.0 eq.) in dioxane and water (9 mL/1 mL) was heated at 100° C. overnight under N2 protection, then cooled and concentrated. The resulting residue was purified via flash column chromatography (PE/EA=3/1, v/v) to (2,6-difluoro-3-hydroxyphenyl)(3-phenylquinoxalin-6-yl)methanone (15.4 mg, 30%). LRMS (M+H+) m/z calculated 363.1, found 363.0. 1H NMR (CDCl3, 400 MHz) δ 10.38 (s, 1 H), 9.76 (s, 1 H), 8.28-8.40 (m, 5 H), 7.60-7.62 (m, 3 H), 7.18-7.27 (m, 2 H).

후처리

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe resulting residue was purified via flash column chromatography (PE/EA=3/1

출처 및 근거

ORD 기록
ord-a3474e1ec32a481aa87d70190f91c2fe
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249111B2

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