Dimethylamine → HCID 72546828, compound

HRID 2280090Notes

Reaction equation

HRID 2280090 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.[CH3:21][NH:22][CH3:23].[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1>CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C.CC(OC)(C)C.C1C=[C-]C(CCN)=CC=1.Cl[Pd+]>[CH3:21][N:22]([CH3:23])[C:20]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:15]=1[CH:14]=[C:13]1[CH2:12][CH2:11][C:26](=[O:27])[C:25]1=[C:24]2[C:28]1[CH:19]=[CH:20][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 931NaphthaleneHCID 8028TetrahydrofuranHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 72546828HCID 72546828, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 66572931HCID 66572931, compoundCatalyst

Conditions

Temperature
85 °C

Procedure

Follows general procedure E: Ruphos palladacycle (4 mg, 0.0053 mmol), LHMDS (0.42 mL, 0.42 mmol), naphthalene (0.060 g, 0.21 mmol), THF (0.8 mL), and dimethylamine (0.16 mL, 0.32 mmol). The reaction mixture was heated at 85° C. for 1 h, turning the reaction mixture black. The crude product was purified by silica gel flash column chromatography (12 g silica cartridge, 0-15% ethyl acetate/hexanes) to yield the title compound as a dark yellow solid (0.030 g, 48%).

Workup

  1. customThe crude product was purified by silica gel flash column chromatography (12 g silica cartridge, 0-15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-171f347c14294815952a970f450f3a30
Source dataset
uspto-grants-2015_09
Patent number
US09133234B2

Reaction notes

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