Water → (S)-4'-((5-((1-(4-Cyclopropylphenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)-[1,1'-biphenyl]-2-carboxylic acid

HRID 1852041ノート

反応式

HRID 1852041 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]4[C:30]([C:35]([OH:37])=[O:36])=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:25][CH:24]=2)[C:17]([CH3:38])=[C:16]3[CH3:39])=[O:12])[CH3:9])=[CH:4][CH:3]=1.[CH:40]1(B(O)O)[CH2:42][CH2:41]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:40]1([C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([C:29]5[C:30]([C:35]([OH:37])=[O:36])=[CH:31][CH:32]=[CH:33][CH:34]=5)=[CH:27][CH:28]=3)[C:17]([CH3:38])=[C:16]4[CH3:39])=[O:12])[CH3:9])=[CH:4][CH:3]=2)[CH2:42][CH2:41]1

参加物

7

反応物 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 53239853(S)-4'-((5-(1-(4-bromophenyl)ethylcarbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)biphenyl-2-carboxylic acid

生成物 1

HCID 52940480(S)-4'-((5-((1-(4-Cyclopropylphenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)-[1,1'-biphenyl]-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

実験手順

A mixture of (S)-4′-((5-((1-(4-bromophenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylic acid (28 mg, 0.048 mmol), cyclopropylboronic acid (9 mg, 0.10 mmol), Palladium(II) acetate (3.9 mg, 0.017 mmol) tricyclohexylphosphine (10 mg, 0.036 mmol) and potassium phosphate, tribasic, (22 mg, 0.10 mmol) in toluene (2.5 mL) and water (0.3 mL) was heated at 100° C. for 1 h in a Biotage Microwave reactor. The solvent was removed; the residue was filtered and purified by preparative HPLC to yield the title compound as a white solid. ESI-MS (m/z): 543 [M+H]+.

後処理

  1. customThe solvent was removed
  2. filtrationthe residue was filtered
  3. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-79250b5dabb84bf4b59a65402d6b11b3
出典データセット
uspto-grants-2015_02
特許番号
US08957093B2

反応ノート

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