1,3-Dimethyl-2-imidazolidinone → HCID 66665632, compound

HRID 2276520Notes

Reaction equation

HRID 2276520 reaction equation
[Br-].[Li+].[Br-].[CH2:4]([O:6][C:7](=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Zn+])[CH3:5].Cl[C:16]1[N:25]=[C:24]2[C:19]([CH:20]=[C:21]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:23]2)=[CH:18][CH:17]=1.CN1C(=O)N(C)CC1>C1COCC1>[C:32]1([C:21]2[CH:20]=[C:19]3[C:24](=[N:23][C:22]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:25]=[C:16]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]([O:6][CH2:4][CH3:5])=[O:14])[CH:17]=[CH:18]3)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 82050Lithium BromideHCID 86681846HCID 86681846, compoundHCID 178471412HCID 178471412, compound

Product 1

HCID 66665632HCID 66665632, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A mixture comprising lithium bromide (307 mg, 3.54 mmol) and PEPPSi-iPr catalyst (75 mg, 0.110 mmol) in THF (2 ml) was stirred at room temperature for 15 minutes until a solution formed. (6-Ethoxy-6-oxohexyl)zinc(II) bromide (13.26 ml of a 0.5M solution in THF, 6.62 mmol) was added and the mixture was cooled to 0° C. A solution of 7-chloro-2,3-diphenyl-1,8-naphthyridine (step 1) (350 mg, 1.105 mmol) in THF (3 ml)/DMI (1 ml) was added and the resulting mixture was stirred at room temperature for 24 h. The reaction mixture was partitioned between EtOAc and water and the organic portion was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with 0-50% EtOAc in iso-hexane afforded the title product as a yellow oil;

Workup

  1. customformed
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. washthe organic portion was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude product by chromatography on silica eluting with 0-50% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-0e6031d0dc8b4513bf7acf54f8ae3549
Source dataset
uspto-grants-2015_09
Patent number
US09132127B2

Reaction notes

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