Sodium Carbonate → HCID 53886355、化合物

HRID 380036

反応式

HRID 380036 の反応式
[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:25]=[C:26]([CH:29]=[CH:30][C:31]=1[F:32])[C:27]#[N:28].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>[F:32][C:31]1[C:30]([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:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 1235793-Bromo-4-fluorobenzonitrileHCID 54413593(1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

生成物 1

HCID 53886355HCID 53886355、化合物収率 88%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

Prepared according to the method described in Example 12b) from (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxyl]enzeneboronic acid (0.20 g, Example 33), 3-bromo-4-fluorobenzonitrile (0.27 g), 2M aqueous sodium carbonate (0.76 ml) and tetrakis(triphenylphosphine)palladium (0) (0.019 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 (0.22 g).

後処理

  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

出典と根拠

ORDレコード
ord-6de3750c4a394f54a48d2f3953144a3f
出典データセット
uspto-grants-2001_10
特許番号
US06300352B1

関連ノート

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