Ethyl Acetate → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-(pyridine-2-yl)-cyclopropyl)benzo[d]thiazole

HRID 1177555Notes

Reaction equation

HRID 1177555 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[CH:33]=[C:32]([C:34]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)=[CH2:35])[CH:31]=[CH:30][C:28]=3[N:29]=2)=[C:21]([F:42])[CH:20]=1.CCOC(C)=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[CH:33]=[C:32]([C:34]4([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=5)[CH2:1][CH2:35]4)[CH:31]=[CH:30][C:28]=3[N:29]=2)=[C:21]([F:42])[CH:20]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 671118792-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-(pyridin-2-yl)vinyl)benzo[d]thiazole

Product 1

HCID 671118642-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-(pyridine-2-yl)-cyclopropyl)benzo[d]thiazole

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium t-butoxide (36 mg, 0.32 mmol) was added to a solution of trimethyl-sulfoxonium iodide (440 mg, 0.48 mmol) in DMSO to make a 1M solution of ylide. This reaction mixture was stirred for 10 min at RT, then a portion of it (0.64 mL, 0.64 mmol) was added to a solution of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-(pyridine-2-yl)vinyl)-benzo[d]thiazole (134 mg, 0.32 mmol) in THF (0.5 mL). The reaction mixture was stirred overnight, EtOAc was added, and the mixture was washed with water several times, then dried over MgSO4. After concentrating under vacuum, the resulting oil was purified by silica gel chromatography to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-(pyridine-2-yl)-cyclopropyl)benzo[d]thiazole. MS (ESI) m/z: Calculated: 432.1; Observed: 433.1 (M++1).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. washthe mixture was washed with water several times
  3. dry with materialdried over MgSO4
  4. concentrationAfter concentrating under vacuum
  5. customthe resulting oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-93db8ab3914245d6a5685c0ae8c73202
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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