Lithium Hexamethyldisilazide → HCID 178489706, compound

HRID 452097Notes

Reaction equation

HRID 452097 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:20]([CH3:22])C)CCCCC1.C(O)(=O)C(O)=O.[CH3:35][O:36][C:37]1[CH:48]=[CH:47][C:40]([CH2:41][CH:42]2[CH2:46][CH2:45][CH2:44][NH:43]2)=[CH:39][CH:38]=1.C[Si]([N-:53][Si](C)(C)C)(C)C.[Li+]>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]>[CH3:35][O:36][C:37]1[CH:38]=[CH:39][C:40]([CH2:41][CH:42]2[CH2:46][CH2:45][CH2:44][N:43]2[C:18]2[CH:17]=[CH:16][C:15]3[NH:20][CH:22]=[N:53][C:14]=3[CH:19]=2)=[CH:47][CH:48]=1

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 17389656HCID 17389656, compound

Product 1

HCID 178489706HCID 178489706, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The compound was synthesized starting from 5 (6)-bromobenzimidazole (200 mg; 1 mmol; 1 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 2-(4-methoxybenzyl)-pyrrolidine oxalate (337 mg; 1.2 mmol; 1.2 eq.) and lithiumbis(trimethylsilyl)amide (1 M solution in THF; 3.3 ml; 3.3 mmol; 3.3 eq.); yield: 0.06 g (1.9%); MS m/z: 308.2 [M+H]+; HPLC (Gradient 3): rt 14.07 (98.9%)

Workup

  1. customThe compound was synthesized

Sources & evidence

ORD record
ord-d818c50b302d49448b91583a99b0ed52
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Reaction notes

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