HCID 68858146, compound → HCID 57752607, compound

HRID 226118Notes

Reaction equation

HRID 226118 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]2[S:6][C:7]([C:10]3[N:14]4[N:15]=[C:16]([CH3:26])[CH:17]=[C:18]([C:19]([CH2:23][CH2:24][CH3:25])=[CH:20][CH2:21][CH3:22])[C:13]4=[N:12][C:11]=3[CH3:27])=[C:8]([CH3:9])[C:4]=2[CH:3]=1>[Pd].CO>[F:1][C:2]1[CH:29]=[CH:28][C:5]2[S:6][C:7]([C:10]3[N:14]4[N:15]=[C:16]([CH3:26])[CH:17]=[C:18]([CH:19]([CH2:20][CH2:21][CH3:22])[CH2:23][CH2:24][CH3:25])[C:13]4=[N:12][C:11]=3[CH3:27])=[C:8]([CH3:9])[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 68858146HCID 68858146, compound

Product 1

HCID 57752607HCID 57752607, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(5-fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-8-(1-propyl-but-1-enyl)-imidazo[1,2-b]pyridazine (23 mg, 0.06 mmol), MeOH (19 mL), and 10% Pd—C (69 mg) is hydrogenated at 30 psi at room temperature for 2 hours. The mixture is filtered through celite, washed with EtOAC and concentrated to dryness to give the title compound (20.5 mg, 89%) %). 1H NMR (CDCl3): δ 7.8 (dd, J=4.8, 8.5 Hz, 1H), 7.5 (dd, J=2.5, 9.7 Hz, 1H), 7.2 (m, 1H), 6.9 (s, 1H), 3.69 (s, 1H), 2.62 (s, 3H), 2.58 (s, 3H), 2.4 (m, 2H), 2.3 (s, 3H), 1.8 (m, 4H), 1.29 (m, 4H), 0.93 (t, J=7.1, 6H) ppm. Mass spectrum (m/e): 410 (M+1).

Workup

  1. filtrationThe mixture is filtered through celite
  2. washwashed with EtOAC
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ddb619d7f4784d04a3985a6f6f96eb00
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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