1,2-Dichloroethane → 4-(2,2-Difluoro-1-phenylethylcarbamoyl)-3-fluorophenylboronic acid

HRID 595797ノート

反応式

HRID 595797 の反応式
[B:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([F:13])[CH:5]=1)([OH:3])[OH:2].[F:14][CH:15]([F:24])[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH2:17].CCN(C(C)C)C(C)C.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CN(C=O)C>[F:14][CH:15]([F:24])[CH:16]([NH:17][C:8]([C:7]1[CH:11]=[CH:12][C:4]([B:1]([OH:2])[OH:3])=[CH:5][C:6]=1[F:13])=[O:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

9

反応物 6

HCID 111,2-DichloroethaneHCID 311Citric AcidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27632014-Carboxy-3-fluorophenylboronic acidHCID 452826412,2-Difluoro-1-phenylethan-1-amine

生成物 1

HCID 1235349834-(2,2-Difluoro-1-phenylethylcarbamoyl)-3-fluorophenylboronic acid

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-borono-2-fluorobenzoic acid (200 mg, 1.087 mmol), 2,2-difluoro-1-phenylethanamine (232 mg, 1.196 mmol), and DIEA (0.570 mL, 3.26 mmol) in THF (3.866 mL) and DMF (0.483 mL) was added HOAt (296 mg, 2.175 mmol) and EDC (521 mg, 2.72 mmol). After 3 h stirring at room temperature, 10% citric acid solution was added (pH ˜3) and extracted with 2-methyl THF and EtOAc (1:1). The organic layers were dried over anhydrous Na2SO4, filtered, and concentrated. The crude 4-(2,2-difluoro-1-phenylethylcarbamoyl)-3-fluorophenylboronic acid was obtained (90%) and used for the next step without purification. LCMS (m/z): 375.3 (MH+), 0.48 min.

後処理

  1. extractionextracted with 2-methyl THF and EtOAc (1:1)
  2. dry with materialThe organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-10da6daac0da476486f9959ec4a2ca54
出典データセット
uspto-grants-2016_01
特許番号
US09242996B2

反応ノート

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