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Potassium Carbonate → 2-methoxy-5-((2-(4-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)isonicotinaldehyde

HRID 1471696
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HRID 1471696 반응식
Br[C:2]1[C:7]([CH2:8][O:9][C:10]2[C:15]([CH:16]=[O:17])=[CH:14][C:13]([O:18][CH3:19])=[N:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:20][C:21]1[CH:22]=[N:23][N:24]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][O:30]2)[C:25]=1B(O)O.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>[CH3:19][O:18][C:13]1[CH:14]=[C:15]([C:10]([O:9][CH2:8][C:7]2[C:2]([C:25]3[N:24]([CH:29]4[CH2:34][CH2:33][CH2:32][CH2:31][O:30]4)[N:23]=[CH:22][C:21]=3[CH3:20])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:11][N:12]=1)[CH:16]=[O:17]
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 68490911[4-methyl-1-(oxan-2-yl)-1H-pyrazol-5-yl]boronic acidHCID 716217595-((2-Bromopyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde

생성물 1

HCID 866907482-methoxy-5-((2-(4-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)isonicotinaldehyde수율 87%

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-((2-bromopyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde (100 mg, 0.31 mmol, 1 equiv), 4-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-ylboronic acid (98 mg, 0.47 mmol, 1.5 equiv), Pd(PPh3)4 (70 mg, 0.06 mmol, 0.2 equiv), K2CO3 (171 mg, 1.24 mmol, 4 equiv) in a 5 mL microwave tube was 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-((2-(4-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)isonicotinaldehyde (110 mg, 87%) as a colorless oil. LRMS (M+H+) m/z 409.2.

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-a24c653b5f6948dfb8f097cd0fbeea7a
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09012450B2

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