HCID 58886656, compound → HCID 58886658, compound

HRID 1766806Notes

Reaction equation

HRID 1766806 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=2[F:25])=[C:7]([F:16])[C:8]2[N:9]([C:11]([C:14]#[CH:15])=[CH:12][N:13]=2)[CH:10]=1)=[O:4]>[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:6]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=2[F:25])=[C:7]([F:16])[C:8]2[N:9]([C:11]([CH2:14][CH3:15])=[CH:12][N:13]=2)[CH:10]=1)=[O:4]

Participants

3

Reactant 1

HCID 58886656HCID 58886656, compound

Product 1

HCID 58886658HCID 58886658, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 3-ethynyl-8-fluoro-7-(2-fluoro-4-methyl-phenylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (16 mg, 0.047 mmol) and 10% Pd/C (5 mg) under an atmosphere of hydrogen (balloon) was stirred vigorously for one hour. The mixture was filtered through a plug of rinsing with dichloromethane and concentrated to provide the desired product (14 mg, 86%) as a yellow foam. MS APCI (+) m/z 346 (M+1) detected. 1H NMR (400 MHz, CDCl3) δ 8.51 (s, 1H), 8.31 (s, 1H), 7.38 (s, 1H), 6.91 (d, 1H), 6.84 (s, 2H), 3.97 (s, 3H), 2.86 (q, 2H), 2.30 (s, 3H), 1.43 (t, 3H).

Workup

  1. filtrationThe mixture was filtered through a plug
  2. washof rinsing with dichloromethane
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b5a6bc844f6845389bb0eeeeb84bea02
Source dataset
uspto-grants-2007_06
Patent number
US07230099B2

Reaction notes

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