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3-Pyridinylboronic acid → 3-(4-Fluorobenzyl)-1-methyl-6-[(1-pyridin-3-ylimidazo[1,5-a]pyridin-3-yl)carbonyl]quinazoline-2,4(1H,3H)-dione

HRID 409548
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HRID 409548 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:21]1[N:22]=[C:23]([C:30]([C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[N:38]([CH3:42])[C:37](=[O:43])[N:36]([CH2:44][C:45]2[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=2)[C:35]3=[O:52])=[O:31])[N:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=12>O.CN(C=O)C.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>[F:51][C:48]1[CH:49]=[CH:50][C:45]([CH2:44][N:36]2[C:35](=[O:52])[C:34]3[C:39](=[CH:40][CH:41]=[C:32]([C:30]([C:23]4[N:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]5=[C:21]([C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)[N:22]=4)=[O:31])[CH:33]=3)[N:38]([CH3:42])[C:37]2=[O:43])=[CH:46][CH:47]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 27343783-Pyridinylboronic acidHCID 23436936Potassium phosphate dihydrateHCID 866834546-[(1-Bromoimidazo[1,5-a]pyridin-3-yl)carbonyl]-3-(4-fluorobenzyl)-1-methylquinazoline-2,4(1H,3H)-dione

생성물 1

HCID 565975113-(4-Fluorobenzyl)-1-methyl-6-[(1-pyridin-3-ylimidazo[1,5-a]pyridin-3-yl)carbonyl]quinazoline-2,4(1H,3H)-dione수율 87.9%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매
HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

0.04 g (0.32 mmol) of 3-pyridylboronic acid, 0.2 g (0.81 mmol) of potassium phosphate dihydrate dissolved in 0.29 ml of water, and 6.2 mg (0.01 mmol) of tetrakis(triphenylphosphine)palladium are added to 0.15 g (0.27 mmol) of 6-[(1-bromoimidazo[1,5-a]pyridin-3-yl)carbonyl]-3-(4-fluorobenzyl)-1-methylquinazoline-2,4(1H,3H)-dione in 3 ml of DMF under an inert argon atmosphere. The reaction medium is microwave-heated at 150° C. for 20 minutes. After filtration over talc, the reaction medium is concentrated under reduced pressure. The residue obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (95/5) mixture. 0.12 g of a yellow solid is obtained.

후처리

  1. filtrationAfter filtration over talc
  2. concentrationthe reaction medium is concentrated under reduced pressure
  3. customThe residue obtained
  4. customis purified by silica gel column chromatography, elution

출처 및 근거

ORD 기록
ord-9f9e3cffaddc45e397c7f27535a25d93
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08759344B2

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