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Toluene → HCID 24856033、化合物

HRID 606008
ノート
印刷プレビュー

反応式

HRID 606008 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][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[OH:18][CH2:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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.ClCCl.C(#N)C>[C:14]1([CH3:17])[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([C:24]4[CH:25]=[C:20]([CH2:19][OH:18])[CH:21]=[CH:22][CH:23]=4)=[CH:7][N:6]3[CH:8]=2)=[CH:12][CH:13]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 14128386-Bromo-2-(4-methylphenyl)imidazo[1,2-a]pyridineHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acid

生成物 1

HCID 24856033HCID 24856033、化合物収率 45.7%

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 6342Acetonitrile溶媒
HCID 6344Dichloromethane溶媒

実験手順

Under a stream of nitrogen, 200 mg of 6-bromo-2-p-tolylimidazo[1,2-a]pyridine, 160 mg of 3-(hydroxymethyl)phenylboronic acid and 24 mg of tetrakis(triphenylphosphine)palladium are placed in a microwave tube containing 2 ml of toluene degassed beforehand under a stream of nitrogen, 2 ml of acetonitrile and 2 ml of a 2M solution of sodium carbonate. The tube is placed in a microwave apparatus and irradiated at 150° C. for 15 min. The organic phase is separated and dried and the filtrate is concentrated under reduced pressure. The residue obtained is taken up with 6 ml of dichloromethane. The precipitate is recovered by filtration, washed with dichloromethane and dried in a desiccator under reduced pressure. 100 mg of compound are obtained. Mp=171-173° C. 1H NMR (DMSO-d6, δ in ppm): 2.32 (s, 3H); 4.57 (d, J=5.6 Hz, 2H); 5.23 (t, J=5.7 Hz, 1H); from 7.19 to 7.67 (m, 8H); 7.84 (d, J=8 Hz, 2H); 8.32 (s, 1H); 8.82 (m, 1H). M+H=315.

後処理

  1. customirradiated at 150° C. for 15 min
  2. customThe organic phase is separated
  3. customdried
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue obtained
  6. filtrationThe precipitate is recovered by filtration
  7. washwashed with dichloromethane
  8. customdried in a desiccator under reduced pressure

出典と根拠

ORDレコード
ord-01b63b4a7dbc458aaf8360f5ba84c9d8
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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