HCID 67112004, compound → HCID 67111689, compound

HRID 1177476Notes

Reaction equation

HRID 1177476 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:26]=[CH:27]/[C:28]([O:30][CH3:31])=[O:29])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.[H][H]>C1COCC1.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][CH2:19]1)[N:11]=2

Participants

5

Reactant 2

HCID 67112004HCID 67112004, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67111689HCID 67111689, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of (E)-methyl 3-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)acrylate (0.116 g, 0.269 mmol) and Pd/C 10%, 50% water (0.115 g, 0.108 mmol) in 2 mL THF was treated with a hydrogen balloon with rapid stirring for 3 h. The reaction mixture was flushed with nitrogen, diluted with DCM, filtered through celite, rinsing with DCM. The filtrate was concentrated in vacuo to give methyl 3-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)propanoate as a white solid. MS (ESI) m/z; calculated: 432.1; Observed: 433.1 (M++1).

Workup

  1. customThe reaction mixture was flushed with nitrogen
  2. additiondiluted with DCM
  3. filtrationfiltered through celite
  4. washrinsing with DCM
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-87fcf2fe3f0f462fa889cacc8dc20a1b
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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