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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
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HRID 2090088 반응식
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]
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반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 35474222-Isopropoxy-5-methylphenylboronic acidHCID 25152389N-(4-Bromobenzyl)-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide

생성물 1

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

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 702Ethanol용매
HCID 1140Toluene용매

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온도
150 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-97b7c0f296fb4b48b72a6907de84b639
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08436028B2

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