Cesium carbonate → Methyl 4-{[2-(dimethylamino)ethyl]amino}benzoate

HRID 1643313Notes

Reaction equation

I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:60][N:61]([CH3:65])[CH2:62][CH2:63][NH2:64]>C(OCC)(=O)C.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].O1CCOCC1>[CH3:60][N:61]([CH3:65])[CH2:62][CH2:63][NH:64][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Methyl 4-iodobenzoate (1 g, 3.82 mmol), XANTPHOS (0.033 g, 0.057 mmol), Pd2(dba)3 (0.035 g, 0.038 mmol), Cs2CO3 (1.741 g, 5.34 mmol) was added to a sealed tube with septa and purged with argon 3×. N,N-dimethyl-1,2-ethanediamine (0.404 g, 4.58 mmol) and 1,4-Dioxane (4 mL) was then added and was stirred at 110° C. for Overnight. The reaction mixture was cooled to room temp and diluted with ethyl acetate and filtered through celite. The organic solvent was concentrated. The product was used without further purification. MS: cal'd 223 (MH+), exp 223 (MH+).

Workup

custompurged with argon 3×
temperatureThe reaction mixture was cooled to room temp
filtrationfiltered through celite
concentrationThe organic solvent was concentrated
customThe product was used without further purification

Sources & evidence

ORD record: ord-b6bee657ad944f6c96dbf5fbaaa25d63
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119685B2

Reaction notes

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