Dibenzylamine → HCID 178420338, compound

HRID 45932

Reaction equation

HRID 45932 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.[CH2:11]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[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]>[CH2:19]([N:18]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:10]=[CH:9][C:5]2[NH:6][CH:7]=[N:8][C:4]=2[CH:3]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 7656DibenzylamineHCID 8028TetrahydrofuranHCID 7852996-Bromo-1H-benzimidazoleHCID 2733832Lithium HexamethyldisilazideHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl

Product 1

HCID 178420338HCID 178420338, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The compound was synthesized starting from 5-bromobenzimidazole (200 mg; 1 mmol; 1 eq.), dibenzylamine (0.231 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 but purified by flash chromatography on silica using a CHCl3/MeOH gradient; Yield: 0.127 g (41%); 314.1 MS m/z: [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 4.67 (s, 4H); 6.70 (br s, 1H); 6.73 (dd, 1H, 4J=2.4 Hz, 3J=8.9 Hz); 7.19-7.23 (m, 2H); 7.28-7.33 (m, 9H); 7.90 (s, 1H); 11.91 (br s, 1H); HPLC (METHOD [A]): rt 14.79 min (99.2%)

Workup

  1. customThe compound was synthesized
  2. custompurified by flash chromatography on silica using a CHCl3/MeOH gradient
  3. customrt 14.79 min (99.2%)

Sources & evidence

ORD record
ord-3c812b5ab0ba448a972a6a1f6eddbd55
Source dataset
uspto-grants-2013_09
Patent number
US08541596B2

Linked notes

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