Sodium Carbonate → (1S,2R)-4-Fluoro-4'-(2-hydroxy-1-methyl-4-pyridin-3-yl-butoxy)biphenyl-3-carbonitrile

HRID 379999

반응식

HRID 379999 반응식
[OH:1][C@H:2]([CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C@H:3]([CH3:14])[O:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1.[C:23]([C:25]1[CH:26]=[C:27](Br)[CH:28]=[CH:29][C:30]=1[F:31])#[N:24].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.C(O)C>[F:31][C:30]1[CH:29]=[CH:28][C:27]([C:8]2[CH:9]=[CH:10][C:5]([O:4][C@@H:3]([CH3:14])[C@H:2]([OH:1])[CH2:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:6][CH:7]=2)=[CH:26][C:25]=1[C:23]#[N:24]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27249005-Bromo-2-fluorobenzonitrileHCID 54413593(1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

생성물 1

HCID 53853615(1S,2R)-4-Fluoro-4'-(2-hydroxy-1-methyl-4-pyridin-3-yl-butoxy)biphenyl-3-carbonitrile

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매

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온도
80 °C

실험 절차

Prepared according to the method described in Example 12 from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.4 g, Example 33), 3-cyano-4-flurobromobenzene (0.399 g), ethanol (10 ml), 2M aqueous sodium carbonate (1.66 ml) and tetrakis(triphenylphosphine)palladium (0) (0.3 g) with heating at 80° C. for 3 hours. After work-up, the residue was purified by normal-phase HPLC eluting a gradient of 0-10% ethanol in dichloromethane to give the title compound as a solid. (0.24 g).

후처리

  1. customPrepared
  2. customAfter work-up, the residue was purified by normal-phase HPLC
  3. washeluting a gradient of 0-10% ethanol in dichloromethane

출처 및 근거

ORD 기록
ord-57fa8a56fc5f40a5ba86f6c4c8cea0aa
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300352B1

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