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Potassium Carbonate → 2-methoxy-5-((3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)isoquinolin-4-yl)methoxy)isonicotinaldehyde

HRID 1471701
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HRID 1471701 반응식
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1[CH2:12][O:13][C:14]1[C:19]([CH:20]=[O:21])=[CH:18][C:17]([O:22][CH3:23])=[N:16][CH:15]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:24][Si:25]([CH3:39])([CH3:38])[CH2:26][CH2:27][O:28][CH2:29][N:30]1[C:34](B(O)O)=[CH:33][CH:32]=[N:31]1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[CH3:23][O:22][C:17]1[CH:18]=[C:19]([C:14]([O:13][CH2:12][C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[N:3][C:2]=2[C:34]2[N:30]([CH2:29][O:28][CH2:27][CH2:26][Si:25]([CH3:39])([CH3:38])[CH3:24])[N:31]=[CH:32][CH:33]=2)=[CH:15][N:16]=1)[CH:20]=[O:21]
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 21874652(1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)boronic acidHCID 866907505-((3-Chloroisoquinolin-4-yl)methoxy)-2-methoxyisonicotinaldehyde

생성물 1

HCID 866907522-methoxy-5-((3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)isoquinolin-4-yl)methoxy)isonicotinaldehyde수율 40.8%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6228Dimethylformamide용매

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온도
125 °C

실험 절차

To a mixture of 5-((3-chloroisoquinolin-4-yl)methoxy)-2-methoxyisonicotinaldehyde (18 mg, 0.05 mmol, 1 equiv), 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-ylboronic acid (20 mg, 0.08 mmol, 1.5 equiv), Pd(PPh3)4 (12 mg, 0.01 mmol, 0.2 equiv), K2CO3 (30 mg, 0.22 mmol, 4 equiv) in a 5 mL microwave tube were added DMF (2 mL). The mixture was heated 30 min at 125° C. in a microwave reactor. The solid was filtered off and the filtrate was concentrated to dryness. The crude was purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 2-methoxy-5-((3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)isoquinolin-4-yl)methoxy)isonicotinaldehyde (10 mg, 38%) as a white solid. LRMS (M+H+) m/z 491.1.

후처리

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe crude was purified on silica gel using
  4. additiona mixture of EtOAc and hexanes as eluent

출처 및 근거

ORD 기록
ord-8bc0ab7856a7436a9e420185c3792bd8
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09012450B2

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