Dimethylamine → HCID 72547091, compound

HRID 2280092Notes

Reaction equation

HRID 2280092 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]1C[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:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[CH:14]=[C:13]1[CH2:24][CH2:25][C:26](=[O:27])[C:12]1=[CH:11]2

Participants

6

Reactant 4

HCID 674DimethylamineHCID 931NaphthaleneHCID 8028TetrahydrofuranHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 72547091HCID 72547091, compoundYield 50%

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 (0.016 g, 0.072 mmol), THF (0.20 mL), and dimethylamine (54 μL, 0.11 mmol). The reaction mixture was heated at 85° C. for 1.5 h, turning the reaction mixture dark brown over time. The crude product was purified by silica gel flash column chromatography (1.5 cm, 5% ethyl acetate/hexanes) to yield the title compound as a yellow solid (8 mg, 50%).

Workup

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

Sources & evidence

ORD record
ord-2774774f2f1f4ff7bc533165f6e66df3
Source dataset
uspto-grants-2015_09
Patent number
US09133234B2

Reaction notes

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