Lithium Hexamethyldisilazide → 5-Chloro-2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-1,6-naphthyridine

HRID 1678734Notes

Reaction equation

HRID 1678734 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=O)=[C:6]([NH:10]C(=O)OC(C)(C)C)[CH:5]=[CH:4][N:3]=1.[O:18]1[CH2:22][CH2:21][O:20][CH:19]1[C:23]1[CH:28]=[CH:27][C:26]([C:29](=O)[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][CH:24]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:7]=1[CH:8]=[C:30]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:29]([C:26]1[CH:27]=[CH:28][C:23]([CH:19]3[O:20][CH2:21][CH2:22][O:18]3)=[CH:24][CH:25]=1)=[N:10]2

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 52987944tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamateHCID 591643561-(4-(1,3-Dioxolan-2-yl)phenyl)-2-phenylethanone

Product 1

HCID 575007255-Chloro-2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-1,6-naphthyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (2-chloro-3-formylpyridin-4-yl)carbamate (3-1, 30.5 g, 118.9 mmol) and 1-[4-(1,3-dioxolan-2-yl)phenyl]-2-phenylethanone (3-2, 29.0 g, 108.1 mmol) in anhydrous THF (300 mL) at room temperature was added LHMDS (1M in THF, 248 mL) in a stream. The reaction mixture was stirred at room temperature overnight and then it was refluxed for 24 hr. It was cooled and concentrated to a syrup and treated with NaHCO3 (saturated, 50 mL) and water (300 mL) to form a solid which was collected via filtration. The solid was dried, washed with ether and further dried with toluene azeotropically to give the title compound. LRMS m/z (M+1) Calcd: 389.1. Found 389.1.

Workup

  1. temperatureit was refluxed for 24 hr
  2. temperatureIt was cooled
  3. concentrationconcentrated to a syrup
  4. additiontreated with NaHCO3 (saturated, 50 mL) and water (300 mL)
  5. customto form a solid which
  6. filtrationwas collected via filtration
  7. customThe solid was dried
  8. washwashed with ether
  9. dry with materialfurther dried with toluene azeotropically

Sources & evidence

ORD record
ord-1830b602baed4306bcb1c473c6c1ef63
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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