1-Phenethylamine → N-(1-Phenylethyl)-3H-benzo[d]imidazol-5-amine

HRID 45929

反応式

HRID 45929 の反応式
Br[C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][NH:8][C:4]=2[CH:3]=1.[C:11]1([CH:17]([NH2:19])[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:11]1([CH:17]([NH:19][C:2]2[CH:10]=[CH:9][C:5]3[N:6]=[CH:7][NH:8][C:4]=3[CH:3]=2)[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

7

反応物 5

HCID 74081-PhenethylamineHCID 8028TetrahydrofuranHCID 7852996-Bromo-1H-benzimidazoleHCID 2733832Lithium HexamethyldisilazideHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl

生成物 1

HCID 67446293N-(1-Phenylethyl)-3H-benzo[d]imidazol-5-amine

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

The compound was synthesized starting from 5-bromobenzimidazole (200 mg; 1 mmol; 1 eq.), 1-phenylethylamine (145 mg; 0.154 ml; 1.2 mmol; 1.2 eq.), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (9 mg; 0.024 mmol; 0.024 eq.; 2.4 mol %), Pd2 dba3 (9 mg; 0.01 mmol; 0.01 eq.; 1 mol %) and lithiumbis(trimethylsilyl)amide 1 M in THF (2.2 ml; 2.2 mmol; 2.2 eq.) according to method 1; Yield: 0.069 mg (29.1%); MS m/z: 238.1 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 1.42 (d, 3H, 3J=7.0 Hz); 4.44 (quin, 1H, 3J=6.7 Hz); 5.97 (br s, 1H); 6.34 (br s, 1H); 6.59-6.60 (m, 1H); 7.13-7.16 (m, 1H); 7.24-7.28 (m, 3H); 7.38-7.39 (m, 2H); 7.77 (s, 1H); 11.74 (br s, 1H); HPLC (METHOD [A]): rt 11.42 min (90.3%)

後処理

  1. customThe compound was synthesized
  2. customrt 11.42 min (90.3%)

出典と根拠

ORDレコード
ord-9813c14b57ec4bf1bfa0a81c10400930
出典データセット
uspto-grants-2013_09
特許番号
US08541596B2

関連ノート

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