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

HRID 45930

Reaction equation

HRID 45930 reaction equation
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][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH2:17])=[CH:14][CH:13]=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]>[CH3:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH:17][C:2]2[CH:10]=[CH:9][C:5]3[N:6]=[CH:7][NH:8][C:4]=3[CH:3]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 660354-MethylbenzylamineHCID 7852996-Bromo-1H-benzimidazoleHCID 2733832Lithium HexamethyldisilazideHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl

Product 1

HCID 67443866N-(4-Methylbenzyl)-3H-benzo[d]imidazol-5-amine

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The compound was synthesized starting from 5-bromobenzimidazole (200 mg; 1 mmol; 1 eq.), 4-methylbenzylamine (145 mg; 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: 0.058 g (24.5%); MS m/z: 238.3 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 2.24 (s, 3H); 4.21 (s, 2H); 5.97 (br s, 1H); 6.49 (s, 1H); 6.59 (dd, 1H, 4J=1.8 Hz, 3J=8.5 Hz); 7.08-7.10 (m, 2H); 7.24-7.26 (m, 3H); 7.82 (s, 1H); 11.82 (br s, 1H); HPLC (METHOD [A]): rt 11.87 min (96.2%)

Workup

  1. customThe compound was synthesized
  2. customrt 11.87 min (96.2%)

Sources & evidence

ORD record
ord-2d77b74cc6434d7190c9d8c6daa3f1f6
Source dataset
uspto-grants-2013_09
Patent number
US08541596B2

Linked notes

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