Water → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine

HRID 1177433Notes

Reaction equation

HRID 1177433 reaction equation
O.[O:2]1[CH2:7][CH2:6][CH2:5][O:4][CH:3]1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]3[C:21]([N:22]=2)=[CH:20][CH:19]=[C:18]([C:23]2([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:28][CH2:27][CH:26]=[CH:25][CH2:24]2)[N:17]=3)=[C:10]([F:35])[CH:9]=1>[Pd].C1COCC1>[O:4]1[CH2:5][CH2:6][CH2:7][O:2][CH:3]1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]3[C:21]([N:22]=2)=[CH:20][CH:19]=[C:18]([C:23]2([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[N:17]=3)=[C:10]([F:35])[CH:9]=1

Participants

5

Reactant 2

HCID 962WaterHCID 671117662-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclohex-3-enyl)thiazolo[5,4-b]pyridine

Product 1

HCID 671117162-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10% palladium on carbon, 50% water wet (0.33 g, 0.31 mmol) and 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclohex-3-enyl)thiazolo[5,4-b]pyridine (0.492 g, 1.0 mmol) under nitrogen was treated with 10 mL THF and exposed to 1 atm H2 gas via balloon. The reaction mixture was allowed to stir 36 h, then flush with nitrogen, filter, rinsing with DCM. The filtrate was concentrated in vacuo to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine as a light yellow solid. MS (ESI) m/z: Calculated: 474.2; Observed: 475.1 (M++1).

Workup

  1. customflush with nitrogen
  2. filtrationfilter
  3. washrinsing with DCM
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7109e6c9e7c245bfabbcd8897b53a926
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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