Ethyl 2-iodobenzoate → HCID 23291926, compound

HRID 365528Notes

Reaction equation

HRID 365528 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:16])([CH3:15])[CH2:7][CH2:8][N:9]2[CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.CC([O-])(C)C.[Na+].I[C:24]1[CH:34]=[CH:33][CH:32]=[CH:31][C:25]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]>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>[CH:12]([N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:33]3[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:34]=3)[CH:11]=2)[C:6]([CH3:15])([CH3:16])[CH2:7][CH2:8]1)([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 2829347Ethyl 2-iodobenzoateHCID 23291920HCID 23291920, compound2×HCID 23676156Sodium t-butoxide

Product 1

HCID 23291926HCID 23291926, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

7-Amino-1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinoline (Compound 33, 130 mg, 0.5954 mmol) was placed into the round bottom flask charged with argon and Pd2 (dab)3 (1.363 mg, 0.25 mol %), and BINAP (2.78 mg, 0.75 mol %) were added, followed by addition of NaOtBu (80.11 mg, 0.8335 mmol), ethyl iodobenzoate (230 mg, 0.8335 mmol) and toluene (3 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=0.30) to give the title compound (90.3 mg, 41%) as a solid: PNMR (300 MHz, CDCl3): δ1.20 (d, 6 H, J=6.6 Hz), 1.28 (s, 6 H), 1.38 (t, 3 H, J=7.1 Hz), 1.71 (t, 2 H, J=6.0 Hz), 3.19 (t, 2 H, J=6.0 Hz), 4.02 (sp, 1 H, J=6.6 Hz), 4.34 (q, 2 H, J=7.1 Hz), 5.92 (s, 1 H), 6.43 (dd, 1 H, J=8.1, 2.1 Hz), 6.50 (d, 1 H, J=2.1 Hz), 6.97 (d, 2 H, J=8.7 Hz), 7.14 (d, 1 H, J=8.1 Hz), 7.90 (d, 2 H, J=8.7 Hz).

Workup

  1. additionwere added
  2. temperaturecooled to room temperature
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.30)

Sources & evidence

ORD record
ord-c99241a0d7cb4cb8a3bb5883077c6d50
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

Loading…