Sodium Carbonate → 5-(2-Phenoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 1432325

反応式

HRID 1432325 の反応式
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17](Br)[CH:18]=[C:13]3[C:12]([C:20]#[N:21])=[CH:11]2)(=O)=O)C=CC=CC=1.[O:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>CCO.C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:22]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=1[C:17]1[CH:18]=[C:13]2[C:12]([C:20]#[N:21])=[CH:11][NH:10][C:14]2=[N:15][CH:16]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 2773559(2-Phenoxyphenyl)boronic acidHCID 689524475-Bromo-1-(phenylsulfonyl)-1h-pyrrolo[2,3-b]pyridine-3-carbonitrile

生成物 1

HCID 113703495-(2-Phenoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile収率 40.3%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
105 °C

実験手順

A mixture of 8 (40.0 mg, 0.11 mmol), 2-phenoxyphenylboronic acid (35.5 mg, 0.166 mmol), PdCl2(PPh3)2 (7.8 mg, 0.011 mmol), LiCl (14.0 mg, 0.33 mmol), 1M Na2CO3 (276 μL, 0.28 mmol) in EtOH (0.66 mL) and toluene (0.66 mL) was heated at 105° C. for 0.5 h in a sealed reaction tube. Reaction mixture was separated between ethyl acetate and brine. The aqueous layer was extracted with ethyl acetate (2×). The combined organic solutions were concentrated and purified by PTLC using ethyl acetate:hexane (1:1) as eluent to give 9 as a white solid (13.8 mg, 40%); 1H NMR (400 MHz, CDCl3) δ 12.80-12.60 (bs, NH), 8.69 (d, J=2.0 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H), 7.87 (s, 1H), 7.53 (dd, J=7.6, 1.7 Hz, 1H), 7.40 (dt, J=7.5, 1.8 Hz, 1H), 7.29 (m, 3H), 7.06 (m, 2H), 6.94 (m, 2H); MS (CI) m/z 352.8 (MH+MeCN).

後処理

  1. customReaction mixture
  2. customwas separated between ethyl acetate and brine
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  4. concentrationThe combined organic solutions were concentrated
  5. custompurified by PTLC

出典と根拠

ORDレコード
ord-20bc22df7e4b4a9b81ad04896247c8d1
出典データセット
uspto-grants-2009_11
特許番号
US07612086B2

関連ノート

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