Ethyl 2-iodobenzoate → HCID 9951833, compound

HRID 365535Notes

Reaction equation

[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([CH3:15])=[C:11]([NH2:14])[CH:12]=2)[C:7]([CH3:17])([CH3:16])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].CC([O-])(C)C.[Na+].I[C:25]1[CH:35]=[CH:34][CH:33]=[CH:32][C:26]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]>C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH2:30]([O:29][C:27](=[O:28])[C:26]1[CH:32]=[CH:33][C:34]([NH:14][C:11]2[CH:12]=[C:13]3[C:8]([C:7]([CH3:17])([CH3:16])[CH2:6][CH2:5][N:4]3[CH:1]([CH3:3])[CH3:2])=[CH:9][C:10]=2[CH3:15])=[CH:35][CH:25]=1)[CH3:31]

Participants

Conditions

Temperature: 80 °C

Procedure

1-Isopropyl-4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-7-ylamine (Compound 45, 500 mg, 2.152 mmol) was placed into the round bottom flask charged with argon. Pd2 (dab)3 (4.926 mg, 0.25 mol %), and BINAP (10.05 mg, 0.75 mol %) were added, followed by NaOtBu (405.27 mg, 3.012 mmol), ethyl iodobenzoate (831.7 mg, 3.012 mmol) and toluene (8 mL). The resulting mixture was stirred at 80° C. for 3 days, cooled to room temperature, and filtered through Celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.26) to give the title compound (642.76 mg, 79%) as a pale yellow solid:

Workup

additioncharged with argon
temperaturecooled to room temperature
filtrationfiltered through Celite
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.26)

Sources & evidence

ORD record: ord-335a77ad29364426a6546762da612a2d
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127382

Reaction notes

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