Dimethylamine → HCID 72547088, compound

HRID 2280091Notes

Reaction equation

HRID 2280091 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:19]1[CH:20]=[C:15]2[C:16](=[CH:17][CH:18]=1)[C:24]([C:28]1[CH:19]=[CH:20][CH:11]=[CH:12][CH:13]=1)=[C:25]1[C:26](=[O:27])[CH2:11][CH2:12][C:13]1=[CH:14]2

Participants

6

Reactant 4

HCID 674DimethylamineHCID 931NaphthaleneHCID 8028TetrahydrofuranHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 72547088HCID 72547088, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 66572931HCID 66572931, compoundCatalyst

Conditions

Temperature
85 °C

Procedure

Follows general procedure E: Ruphos palladacycle (1.5 mg, 0.0020 mmol), LHMDS (0.14 mL, 0.14 mmol), naphthalene (0.019 g, 0.065 mmol), THF (0.13 mL), and dimethylamine (50 μL, 0.10 mmol). The reaction mixture was heated at 85° C. for 1.5 h, turning reaction mixture brown. The crude product was purified by silica gel flash column chromatography (1.5 cm column, 5% ethyl acetate/hexanes) to yield the title compound as a yellow solid (3 mg, 15%).

Workup

  1. customreaction mixture brown
  2. customThe crude product was purified by silica gel flash column chromatography (1.5 cm column, 5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4b65de3087d24995b7b901c5a24a698d
Source dataset
uspto-grants-2015_09
Patent number
US09133234B2

Reaction notes

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