Sodium bis(trimethylsilyl)amide → 6-(2,4,6-Trifluorophenyl)pyrido[2,3-c]pyridazine-5,7(6H,8H)-dione

HRID 2217967Notes

Reaction equation

HRID 2217967 reaction equation
C(O[C:4]([C:6]1[CH:11]=[CH:10][N:9]=[N:8][C:7]=1[NH:12][C:13](=[O:24])[CH2:14][C:15]1[C:20]([F:21])=[CH:19][C:18]([F:22])=[CH:17][C:16]=1[F:23])=[O:5])C.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[F:21][C:20]1[CH:19]=[C:18]([F:22])[CH:17]=[C:16]([F:23])[C:15]=1[CH:14]1[C:13](=[O:24])[NH:12][C:7]2[N:8]=[N:9][CH:10]=[CH:11][C:6]=2[C:4]1=[O:5]

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 68934065HCID 68934065, compound

Product 1

HCID 597692086-(2,4,6-Trifluorophenyl)pyrido[2,3-c]pyridazine-5,7(6H,8H)-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

The product from Step 2 (2.0 g) was dissolved in dry THF (50 ml), and sodium bis-trimethylsilylamide (17.7 ml of a 11.0M solution in THF) was added dropwise with stirring under nitrogen at 0° C. The reaction was stirred for 3 hours at 0° C. and a yellow precipitate was formed. The reaction was quenched with concentrated hydrochloric acid and then poured into ice water. The solid was filtered, washed with water and air dried to give 6-(2,4,6-trifluorophenyl)-8H-pyrido[2,3-c]pyridazine-5,7-dione as a yellow solid (1.9 2 g), m.p. >330° C., still containing some THF, which was used without further purification.

Workup

  1. stirringThe reaction was stirred for 3 hours at 0° C.
  2. customa yellow precipitate was formed
  3. customThe reaction was quenched with concentrated hydrochloric acid
  4. additionpoured into ice water
  5. filtrationThe solid was filtered
  6. washwashed with water and air
  7. customdried

Sources & evidence

ORD record
ord-51c90b24e6004dcdbb7b8aa8c9b415bf
Source dataset
uspto-grants-2008_08
Patent number
US07410967B2

Reaction notes

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