HCID 10049064, compound → HCID 10369444, compound

HRID 860981Notes

Reaction equation

HRID 860981 reaction equation
[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30](=[O:32])[CH3:31])[CH:25]=4)[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:4])=[O:3].[C:33]1([Mg]Br)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1.C([O-])(O)=O.[Na+]>[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)([OH:32])[CH3:31])[CH:25]=4)[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 10049064HCID 10049064, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 10369444HCID 10369444, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-{3′-[6-(1-methanesulfonyl-1-methyl-ethyl)quinolin-8-yl]-biphenyl-3-yl}-ethanone from Step 1 (1.0 eq.) in THF (0.1M) was added CeCl3 (1.1 eq.). The mixture was put in an ultrasonic bath for 15 min, cooled to −78° C. then phenyl magnesium bromide was added (5.0 eq.). The final mixture was stirred for 12 h at −20° C., poured in NaHCO3 and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 9:1 to 1:9 over 20 min) afforded the title compound as a white solid. 1H NMR (400 MHz, acetone-d6): δ 8.91 (dd, 1H), 8.46 (dd, 1H), 8.29 (d, 1H), 8.18 (d, 1H), 7.97 (d, 1H), 7.86 (d, 1H), 7.68 (dd, 1H), 7.64 (dd, 1H), 7.59–7.50 (m, 5H), 7.48 (d, 1H), 7.39 (t, 1H), 7.27 (t, 2H), 7.16 (t, 1H), 4.73 (s, 1H), 2.72 (s, 3H), 1.99 (s, 6H), 1.98 (s, 3H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ccbd2bdce832463989934d7484735cb3
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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