(2-{3-[6-(1-Methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-benzyloxy}-phenyl)-phenyl-methanone → Cyclopropyl-(2-{3-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-benzyloxy}-phenyl)-phenyl-methanol

HRID 857304Notes

Reaction equation

HRID 857304 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]([CH:37]=[CH:38][CH:39]=3)[CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:30])[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:4])=[O:3].[CH:40]1([Mg]Br)[CH2:42][CH2:41]1>C1COCC1.[NH4+].[Cl-]>[CH:40]1([C:29]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[O:22][CH2:21][C:20]2[CH:37]=[CH:38][CH:39]=[C:18]([C:16]3[CH:17]=[C:8]([C:5]([S:2]([CH3:1])(=[O:4])=[O:3])([CH3:7])[CH3:6])[CH:9]=[C:10]4[C:15]=3[N:14]=[CH:13][CH:12]=[CH:11]4)[CH:19]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[OH:30])[CH2:42][CH2:41]1

Participants

5

Reactant 2

HCID 10152781(2-{3-[6-(1-Methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-benzyloxy}-phenyl)-phenyl-methanoneHCID 178418630HCID 178418630, compound

Product 1

HCID 10129051Cyclopropyl-(2-{3-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-benzyloxy}-phenyl)-phenyl-methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-78 °C

Procedure

To solution of (2-{3-[6-(1-Methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-benzyloxy}-phenyl)-phenyl-methanone (EXAMPLE 74) (1.0 eq) in THF (0.03M) was added CeCl3 (2.7 eq). The resulting mixture was stirred for 1 h, then cooled to −78° C. Cyclopropyl magnesium bromide (0.24M in THF; 4.8 eq) was added and the final mixture was allowed to warm-up to room temperature. After stirring for 1 h the mixture was poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 40 to 100% in 15 min) afforded the title compound as a foam.

Workup

  1. temperatureto warm-up to room temperature
  2. stirringAfter stirring for 1 h the mixture
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5934e5e35de349429c5b065c806e2af1
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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