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Dichloromethane → 4-(((5'-chloro-2'-fluoro-[2,4'-bipyridin]-6-yl)amino)methyl)tetrahydro-2H-pyran-4-carbonitrile

HRID 1623260
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HRID 1623260 반응식
Br[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2([C:16]#[N:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:4][CH:3]=1.BrC1N=C(NCC2CC(C#N)CCO2)C=CC=1.[Cl:35][C:36]1[C:37](B(O)O)=[CH:38][C:39]([F:42])=[N:40][CH:41]=1.C(Cl)Cl>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].COCCOC>[Cl:35][C:36]1[C:37]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]([NH:8][CH2:9][C:10]3([C:16]#[N:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[N:7]=2)=[CH:38][C:39]([F:42])=[N:40][CH:41]=1
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참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 44754822(5-Chloro-2-fluoropyridin-4-yl)boronic acidHCID 581272764-((6-bromopyridin-2-yl-amino)methyl)tetrahydro-2H-pyran-4-carbonitrileHCID 86689267((6-bromopyridin-2-yl-amino)methyl)tetrahydro-2H-pyran-4-carbonitrile

생성물 1

HCID 581271824-(((5'-chloro-2'-fluoro-[2,4'-bipyridin]-6-yl)amino)methyl)tetrahydro-2H-pyran-4-carbonitrile수율 75%

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 80711,2-Dimethoxyethane용매

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온도
110 °C

실험 절차

A mixture of 4-((6-bromopyridin-2-yl-amino)methyl)tetrahydro-2H-pyran-4-carbonitrile (Intermediate S, 410 mg, 1.384 mmol), 5-chloro-2-fluoropyridin-4-ylboronic acid (362.2 mg, 2.07 mmol), PdCl2(dppf).CH2Cl2 adduct (113 mg, 0.14 mmol), DME (5 Ml) and 2 M aqueous Na2CO2 (1.75 Ml, 3.5 mmol) was sealed and stirred at 110° C. for 20 min using microwave reactor. After cooling to room temperature the mixture was extracted with EtOAc (35 Ml), filtered and concentrated in vacuo. The crude material was purified by column chromatography [silica gel, 24 g, EtOAc/hexane=5/100 to 50/50] to provide 4-((5′-chloro-2′-fluoro-2,4′-bipyridin-6-ylamino)methyl)tetrahydro-2H-pyran-4-carbonitrile (360 mg, 75% yield). LCMS (m/z): 347 [M+H]+; retention time=0.814 min.

후처리

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionwas extracted with EtOAc (35 Ml)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by column chromatography [silica gel, 24 g, EtOAc/hexane=5/100 to 50/50]

출처 및 근거

ORD 기록
ord-9032d38ac11c4bd39a288ac3c33aef1a
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08778951B2

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