Water → HCID 67111466, compound

HRID 1177392Notes

Reaction equation

HRID 1177392 reaction equation
[CH3:1]C(C)([O-])C.[K+].[I-].C[S+](C)(C)=O.[O:13]1[CH2:18][CH2:17][CH2:16][O:15][CH:14]1[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[S:26][C:27]3[C:32]([N:33]=2)=[CH:31][CH:30]=[C:29]([C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH2:35])[N:28]=3)=[C:21]([F:42])[CH:20]=1.O>CS(C)=O.C1COCC1>[O:15]1[CH2:16][CH2:17][CH2:18][O:13][CH:14]1[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[S:26][C:27]3[C:32]([N:33]=2)=[CH:31][CH:30]=[C:29]([C:34]2([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH2:1][CH2:35]2)[N:28]=3)=[C:21]([F:42])[CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 671118192-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylvinyl)thiazolo[5,4-b]pyridine

Product 1

HCID 67111466HCID 67111466, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of potassium tert-butoxide (4.02 g, 35.8 mmol) in 100 mL DMSO under nitrogen was added trimethyl sulfoxonium iodide (7.89 g, 35.8 mmol) in 4 portions over about 20 minutes. 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylvinyl)thiazolo[5,4-b]pyridine (10.0 g, 23.9 mmol) was suspended in 150 mL THF and filtered through a glass frit, rinsing with 25 mL THF. The filtrate was added to the reaction dropwise very slowly from an addition funnel over 1.5-2 h. The resulting orange reaction was allowed to stir 30 min, at which point the THF was removed in vacuo, resulting in a precipitate. Water and ice was added slowly with stirring (approximately 400 mL total). The solid was isolated by filtration rinsing with water and MeOH. The solid was dried in vacuo to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine as a light orange solid. MS (ESI) m/z: Calculated: 432.1; Observed: 433.1 (M++1).

Workup

  1. filtrationfiltered through a glass frit
  2. washrinsing with 25 mL THF
  3. additionThe filtrate was added to the reaction dropwise very slowly from an addition funnel over 1.5-2 h
  4. customThe resulting orange reaction
  5. customwas removed in vacuo
  6. customresulting in a precipitate
  7. customThe solid was isolated by filtration
  8. washrinsing with water and MeOH
  9. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-b2e6cab1af4e4aff9ba8d3cf7a7bbd3e
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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