Tetrahydrofuran → N-(3,4-Dimethoxybenzyl)-3H-benzo[d]imidazol-5-amine

HRID 45927

反応式

HRID 45927 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.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:16][NH2:17].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]>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:16][NH:17][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][NH:8][C:4]=2[CH:3]=1

参加物

7

反応物 5

HCID 8028TetrahydrofuranHCID 79832VeratrylamineHCID 7852996-Bromo-1H-benzimidazoleHCID 2733832Lithium HexamethyldisilazideHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl

生成物 1

HCID 67444547N-(3,4-Dimethoxybenzyl)-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.), 3,4-dimethoxybenzylamine (201 mg; 0.181 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: 0.064 g (22.6%); MS m/z: 284.1 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 3.69 (s, 3H); 3.71 (s, 3H); 4.17 (d, 2H, 3J=5.8 Hz); 5.96 (br s, 1H); 6.48 (br s, 1H); 6.58-6.60 (m, 1H); 6.85-6.89 (m, 2H); 6.99 (s, 1H); 7.27-7.29 (m, 1H); 7.80 (s, 1H); 11.78 (br s, 1H); HPLC (METHOD [A]): rt 8.92 min (100%)

後処理

  1. customThe compound was synthesized
  2. customrt 8.92 min (100%)

出典と根拠

ORDレコード
ord-900fc40b0b2a41c596b389099d73e2a8
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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