Pivalaldehyde → HCID 57929850, compound

HRID 1930040Notes

Reaction equation

HRID 1930040 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]#[C:10][C:11]1[N:12]=[N:13][C:14]([NH:17][NH2:18])=[CH:15][CH:16]=1.[CH:19](=O)[C:20]([CH3:23])([CH3:22])[CH3:21].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[C:20]([C:23]1[N:13]2[N:12]=[C:11]([C:10]#[C:9][C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])[CH:16]=[CH:15][C:14]2=[N:17][N:18]=1)([CH3:22])([CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 12417PivalaldehydeHCID 12217721Iodo benzene diacetateHCID 57929956HCID 57929956, compound

Product 1

HCID 57929850HCID 57929850, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-((2,4-difluorophenyl)ethynyl)-6-hydrazinylpyridazine (0.60 g, 2.4 mmol) and pivalaldehyde (0.31 g, 3.7 mmol) were dissolved in DCM (8 mL) and were stirred at ambient temperature for about 2 h. Iodobenzene diacetate (0.86 g, 2.7 mmol) was added and was stirred for about 2 h at ambient temperature. The reaction mixture was concentrated in vacuo and was purified by silica gel chromatography using DCM/MeOH (gradient, 0-2% MeOH) to afford the title compound (0.49 g, 64%): LC/MS (Table 1, Method a) Rt=2.50 min; MS m/z: 313.2 (M+H)+.

Workup

  1. stirringwas stirred for about 2 h at ambient temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-bb65a0c310b44d82b489c354e6232235
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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