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6-Bromo-2-phenylimidazo[1,2-a]pyridine → [4-(2-Phenylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol

HRID 606005
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HRID 606005 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[OH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>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.C(#N)C>[C:11]1([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([C:22]4[CH:23]=[CH:24][C:19]([CH2:18][OH:17])=[CH:20][CH:21]=4)=[CH:7][N:6]3[CH:8]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 6234306-Bromo-2-phenylimidazo[1,2-a]pyridineHCID 27347064-(Hydroxymethyl)benzeneboronic acid

생성물 1

HCID 24855995[4-(2-Phenylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol수율 31.5%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

150 mg of 6-bromo-2-phenylimidazo[1,2-a]pyridine, 125 mg of 4-(hydroxymethyl)phenylboronic acid, 19 mg of tetrakis(triphenylphosphine)palladium and 2 ml of acetonitrile are placed in a microwave tube. Under a stream of nitrogen, 2 ml of nitrogen-degassed toluene and then 2 ml of a 2M solution of sodium carbonate are added thereto. The tube is placed in a microwave device and irradiated at 150° C. for 15 min. The organic phase is recovered, dried and then concentrated under reduced pressure. The residue is taken up with diisopropyl ether and the precipitate is recovered by filtration, washed and dried. It is purified by recrystallization from n-butanol. 52 mg of compound are obtained. Mp=238-240° C. 1H NMR (DMSO-d6, δ in ppm): 4.54 (d, J=5.5 Hz, 2H); 5.2 (t, J=5.6 Hz, 1H); from 7.24 to 7.73 (m, 9H); 7.96 (m, 2H); 8.36 (s, 1H); 8.84 (t, J=1.3 Hz, 1H). M+H=301.

후처리

  1. customUnder a stream of nitrogen, 2 ml of nitrogen-degassed toluene
  2. addition2 ml of a 2M solution of sodium carbonate are added
  3. customirradiated at 150° C. for 15 min
  4. customThe organic phase is recovered
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. filtrationthe precipitate is recovered by filtration
  8. washwashed
  9. customdried
  10. customIt is purified by recrystallization from n-butanol

출처 및 근거

ORD 기록
ord-f7701a5c209f4245be042274300ca1a1
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07915284B2

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