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Water → 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-[(2'-isopropoxy-5'-methylbiphenyl-4-yl)methyl]benzamide

HRID 2090088
ノート
印刷プレビュー

反応式

HRID 2090088 の反応式
C(=O)([O-])[O-].[Na+].[Na+].[CH:7]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1B(O)O)([CH3:9])[CH3:8].Br[C:22]1[CH:51]=[CH:50][C:25]([CH2:26][NH:27][C:28](=[O:49])[C:29]2[CH:34]=[CH:33][C:32]([C:35]3[O:36][C:37]4[C:43]([CH:44]([CH3:46])[CH3:45])=[CH:42][C:41]([C:47]#[N:48])=[CH:40][C:38]=4[N:39]=3)=[CH:31][CH:30]=2)=[CH:24][CH:23]=1.O>C1(C)C=CC=CC=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(O)C>[C:47]([C:41]1[CH:42]=[C:43]([CH:44]([CH3:46])[CH3:45])[C:37]2[O:36][C:35]([C:32]3[CH:33]=[CH:34][C:29]([C:28]([NH:27][CH2:26][C:25]4[CH:50]=[CH:51][C:22]([C:12]5[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]=5[O:10][CH:7]([CH3:9])[CH3:8])=[CH:23][CH:24]=4)=[O:49])=[CH:30][CH:31]=3)=[N:39][C:38]=2[CH:40]=1)#[N:48]
参加物反応条件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 962WaterHCID 10340Sodium CarbonateHCID 35474222-Isopropoxy-5-methylphenylboronic acidHCID 25152389N-(4-Bromobenzyl)-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide

生成物 1

HCID 251523904-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-[(2'-isopropoxy-5'-methylbiphenyl-4-yl)methyl]benzamide

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 702Ethanol溶媒
HCID 1140Toluene溶媒

反応条件

温度
150 °C

実験手順

Sodium carbonate (100 μl of a 2M aqueous solution), (2-isopropoxy-5-methylphenyl)boronic acid (19 mg), and N-(4-bromobenzyl)-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide (24 mg, EXAMPLE 1) were dissolved in toluene (2.1 ml), water (0.6 ml) and ethanol (0.3 ml). To this solution was added tetrakis(triphenylphosphine)palladium(0) (9 mg). The mixture was heated to 150° C. for 25 min via microwave. Upon cooling, the mixture was concentrated in vacuo and then dissolved in dichloromethane (5 ml). The sample was transferred to a Biotage 40M column and purified via flash chromatography, eluting 1 column volume of 100% hexanes followed by a gradient of 0 to 100% ethyl acetate in hexanes over 10 column volume, followed by 100% ethyl acetate for 4 column volumes, to provide the title compound. Mass spectrum (ESI) 544.2 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.35 (d, J=8.4 Hz, 2H), 8.00 (d, J=8.2 Hz, 2H), 7.94 (s, 1H), 7.58 (d, J=8.0 Hz, 2H), 7.52 (s, 1H), 7.40 (d, J=8.0 Hz, 2H), 7.13 (s, 1H), 7.09 (d, J=8.2 Hz, 1H), 6.90 (d, J=8.4 Hz, 2H), 6.47 (t, J=4.6 Hz, 1H), 4.73 (d, J=5.5 Hz, 3H), 4.40 (sept, J=6.2 Hz, 1H), 3.48 (sept, J=7.1 Hz, 1H), 2.32 (s, 3H), 1.46 (d, J=6.9, 6H), 1.24 (d, J=5.9, 6H).

後処理

  1. temperatureUpon cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutiondissolved in dichloromethane (5 ml)
  4. custompurified via flash chromatography
  5. washeluting 1 column volume of 100% hexanes

出典と根拠

ORDレコード
ord-97b7c0f296fb4b48b72a6907de84b639
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08436028B2

反応ノート

読み込み中…

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