Lithium diisopropylamide → HCID 69434605, compound

HRID 349605Notes

Reaction equation

HRID 349605 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][CH3:29])=[C:6]([C:8]2[CH:17]3[CH:12]([CH:13]=[CH:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16]3)[NH:11][C:10](=[O:22])[C:9]=2[S:23][CH2:24][CH:25]2[CH2:27][O:26]2)[CH:7]=1.C([N-]C(C)C)(C)C.[Li+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][CH3:29])=[C:6]([C:8]2[CH:17]3[CH:12]([CH:13]=[CH:14][C:15]([C:18]([F:20])([F:19])[F:21])=[CH:16]3)[NH:11][C:10](=[O:22])[C:9]=2[S:23][CH:24]=[CH:25][CH2:27][OH:26])[CH:7]=1

Participants

4

Reactant 2

HCID 2724682Lithium diisopropylamideHCID 86597528HCID 86597528, compound

Product 1

HCID 69434605HCID 69434605, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

4-(5-Chloro-2-methoxy-phenyl)-3-(3-hydroxy-propenylsulfanyl)-6-trifluoromethyl-4a,8a-dihydro-1H-quinolin-2-one (Ig) was prepared by a base-mediated epoxide rearrangement process. To a solution of VIII (0.2 g, 0.45 mmol) in dry THF (4 mL) at −78° C. under nitrogen was added a THF solution of lithium diisopropylamide (LDA, used as supplied by Aldrich, 1.5 Molar, 0.6 mL). The mixture was stirred at −78° C. for a further 10 min. before it was allowed to warm to room temperature and stirring was continued for another 30 min. It was quenched with saturated solution of NH4Cl, organic residues were extracted into ethyl acetate. The organic layers were combined and dried over MgSO4. Evaporation of solvent gave 0.18 g (90% yield) of the desired product as pale yellow solid, mp 148–150° C. Calcd. for C20H15Cl1F3N1O3S1: C, 54.34; H, 3.42; N, 3.17; F, 12.90; Cl, 8.02. Found: C, 54.34; H, 3.66, N, 2.93; F, 12.80; Cl, 7.95. 1H NMR (300 MHz, DMSO-d6) δ 12.51 (s, 1H), 7.84 (d, J=10.2 Hz, 1H), 7.58–7.54 (m, 2H), 7.30–7.23 (m, 2H), 7.08 (s, 1H), 6.28 (d, J=15.3 Hz, 1H), 5.58 (dt, J=15.3, 5.4 Hz, 1H), 4.74 (t, J=5.7 Hz, 1H), 3.84 (t, J=6.0 Hz, 2H), 3.69 (s, 3H).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirring
  3. waitwas continued for another 30 min
  4. customIt was quenched with saturated solution of NH4Cl, organic residues
  5. extractionwere extracted into ethyl acetate
  6. dry with materialdried over MgSO4
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-837725ac4c48453686fc74151b2aee7a
Source dataset
uspto-grants-2007_02
Patent number
US07179920B2

Reaction notes

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