Ethyl bromoacetate → HCID 90417137, compound

HRID 1748398Notes

Reaction equation

HRID 1748398 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:24])[N:14]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:9][CH:8]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH:12]([CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:13](=[O:24])[N:14]2[C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 2733832Lithium HexamethyldisilazideHCID 90417479HCID 90417479, compound

Product 1

HCID 90417137HCID 90417137, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 7-((3-chlorobenzyl)oxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (34 g, 0.09 mol) in THF (50.09 mL) was added a solution of lithium bis(trimethylsilyl)amide (1.06 M in THF, 99.24 mL, 0.11 mol) at −78° C. The reaction was stirred at that temperature for 30 minutes after which ethyl bromoacetate (9.70 mL, 0.09 mol) was added. The reaction was allowed to warm to ambient temperature, stirred overnight and quenched into water (250 mL). The aqueous layer was extracted with EtOAc (2×50 mL) and the combined organic layers were washed with brine and dried over MgSO4. The organics were concentrated under reduced pressure to afford a yellow-brown oil and carried on crude to the next step. 1H NMR (400 MHz, CDCl3) δ 7.35 (s, 1H), 7.27-7.22 (m, 3H), 7.02 (d, J=8.4 Hz, 1H), 6.59 (dd, J=8.3, 2.5 Hz, 1H), 6.49 (d, J=2.4 Hz, 1H), 4.95 (s, 2H), 4.12 (q, J=7.2 Hz, 2H), 3.06-2.91 (m, 1H), 2.87-2.70 (m, 2H), 2.60 (d, J=7.5 Hz, 1H), 2.37 (d, J=8.9 Hz, 1H), 1.54-1.44 (m, 9H), 1.26-1.19 (m, 3H). [M+H]=374.2.

Workup

  1. additionwas added
  2. customquenched into water (250 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationThe organics were concentrated under reduced pressure
  7. customto afford a yellow-brown oil

Sources & evidence

ORD record
ord-1da557ebda844af49671f7478efe817a
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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