1,2-Dimethoxyethane → HCID 178515614, 화합물

HRID 33554

반응식

HRID 33554 반응식
Br[C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7]([NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[C:14]4[C:19]=3[CH:18]=[C:17]([OH:20])[CH:16]=[CH:15]4)=[N:8][C:4]=2[CH:3]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+].O.C(COC)OC>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCO>[C:23]1([C:2]2[CH:22]=[CH:21][C:5]3[NH:6][C:7]([NH:9][C:10]4[CH:11]=[CH:12][CH:13]=[C:14]5[C:19]=4[CH:18]=[C:17]([OH:20])[CH:16]=[CH:15]5)=[N:8][C:4]=3[CH:3]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

8

반응물 4

HCID 80711,2-DimethoxyethaneHCID 66827Phenylboronic AcidHCID 2735133Sodium Carbonate MonohydrateHCID 178515612HCID 178515612, 화합물

생성물 1

HCID 178515614HCID 178515614, 화합물

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 702Ethanol용매HCID 962Water용매2회

실험 절차

A mixture of 8-(5-bromo-1H-benzo[d]imidazol-2-ylamino)naphthalen-2-ol (18 mg, 0.05 mmol, Example 14), phenylboronic acid (12 mg, 0.1 mmol, Aldrich), PdCl2(PPh3)2 (3.5 mg, 0.005 mmol, Aldrich), Na2CO3.H2O (12 mg, 0.1 mmol), dimethoxyethane (0.35 mL), H2O (0.15 mL) and EtOH (0.1 1 mL) was subjected to microwave irradiation at 120° C. with stirring for 10 min. The reaction mixture was cooled to room temperature, diluted with water (5 mL) and extracted with EtOAc (2×10 mL). The combined organic phases were washed with brine (10 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile) to give the title compound. MS (ESI, pos. ion) m/z: 352 (M+1).

후처리

  1. customirradiation at 120° C.
  2. extractionextracted with EtOAc (2×10 mL)
  3. washThe combined organic phases were washed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile)

출처 및 근거

ORD 기록
ord-3540a1b0460743118b842ff193bedd8a
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429608B2

연결된 노트

불러오는 중…