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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
ノート
印刷プレビュー

反応式

HRID 606005 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f7701a5c209f4245be042274300ca1a1
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07915284B2

反応ノート

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