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

HRID 406174Notes

Reaction equation

HRID 406174 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; LC-MS Rt=1.54 mins; [M+H]+425.3, Method 2minLC_v002

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-933372fc2c32482e8f3bcaefdd54857b
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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