Dimethylamine → HCID 72547092, compound

HRID 2280093Notes

Reaction equation

HRID 2280093 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:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[CH:11]=[C:12]1[C:26](=[O:27])[CH2:25][CH2:24][C:13]1=[CH:14]2

Participants

6

Reactant 4

HCID 674DimethylamineHCID 931NaphthaleneHCID 8028TetrahydrofuranHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 72547092HCID 72547092, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 66572931HCID 66572931, compoundCatalyst

Conditions

Temperature
85 °C

Procedure

Follows general procedure E: Ruphos palladacycle (2 mg, 0.0027 mmol), LHMDS (0.18 mL, 0.18 mmol), naphthalene (0.019 g, 0.088 mmol), THF (0.30 mL), and dimethylamine (0.13 mL, 0.26 mmol). The reaction mixture was heated at 85° C. for 1 h, turning the reaction mixture brown over time. The crude product was purified by silica gel flash column chromatography (1.5 cm, 10% ethyl acetate/hexanes) to yield the title compound as a light brown solid (5 mg, 25%).

Workup

  1. customThe crude product was purified by silica gel flash column chromatography (1.5 cm, 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7519d09a567d414facb460b5a0728c5d
Source dataset
uspto-grants-2015_09
Patent number
US09133234B2

Reaction notes

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