Sodium Carbonate → 4-Phenylnaphthalen-1-amine

HRID 503624

반응식

HRID 503624 반응식
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:12])=[CH:4][CH:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>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].C(Cl)Cl.O1CCOCC1>[C:13]1([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([NH2:12])=[CH:4][CH:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 753034-Bromo-1-naphthylamine

생성물 1

HCID 130872274-Phenylnaphthalen-1-amine

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 312751,4-Dioxane용매

반응 조건

온도
85 °C

실험 절차

A pressure bottle was charged with 4-bromonaphthalen-1-amine (500 mg, 2251 μmol), phenylboronic acid (357 mg, 2927 μmol), PdCl2(dppf)-CH2Cl2 adduct (91.9 mg, 113 μmol), 2.0 M sodium carbonate (2251 μl, 4503 μmol) and 9.0 mL of dioxane. The bottle was sealed and the mixture was heated at 85° C. for 2 h. LCMS showed desired product as the major component. The mixture was diluted with DCM and washed with water. The organic portion was dried, filtered and concentrated. The crude material was purified by silica gel chromatography, DCM to 2% MeOH/DCM to provide 4-phenylnaphthalen-1-amine. MS: [M+H]=220.

후처리

  1. customThe bottle was sealed

출처 및 근거

ORD 기록
ord-de9426c1a1cc433e9111dfc9409438e9
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776857B2

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