Sodium Carbonate → (1S,2R)-3-Chloro-4'-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)biphenyl-4-carbonitrile

HRID 380002

반응식

HRID 380002 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.Br[C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([Cl:32])[CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.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>[Cl:32][C:26]1[CH:25]=[C:24]([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:31]=[CH:30][C:27]=1[C:28]#[N:29]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 70104204-Bromo-2-chlorobenzonitrileHCID 54413593(1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

생성물 1

HCID 57191772(1S,2R)-3-Chloro-4'-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)biphenyl-4-carbonitrile수율 69%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

Prepared according to the method described in Example 12b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.20 g, Example 33), 4-bromo-2-chlorobenzonitrile (0.288 g), 2M aqueous sodium carbonate (0.76 ml) and tetrakis(triphenylphosphine)palladium (0) (0.075 g) in ethanol (5 ml) with heating at 90° C. for 4 hours. After work up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-10% ethanol in dichloromethane to give the title compound as an oil (0.18 g).

후처리

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

출처 및 근거

ORD 기록
ord-1e795bac0e8943e7ad5ad9d9ee0d679e
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300352B1

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