Tetrabutylammonium Fluoride → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylcyclopropyl)-benzo[d]thiazole

HRID 1177444Notes

Reaction equation

HRID 1177444 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[CH:21]=[C:20]([C:22]4([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH2:24][CH:23]4[Si](C)(C)C)[CH:19]=[CH:18][C:16]=3[N:17]=2)=[C:9]([F:35])[CH:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[O:3]1[CH2:4][CH2:5][CH2:6][O:1][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[CH:21]=[C:20]([C:22]4([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)[CH2:23][CH2:24]4)[CH:19]=[CH:18][C:16]=3[N:17]=2)=[C:9]([F:35])[CH:8]=1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 671115752-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-phenyl-2-(trimethylsilyl)cyclopropyl)benzo[d]thiazole

Product 1

HCID 671117192-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylcyclopropyl)-benzo[d]thiazole

Conditions

Temperature
110 °C

Procedure

In a reactor bottle were combined 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-phenyl-2-(trimethylsilyl)cyclopropyl)benzo[d]thiazole (1.305 g, 2.6 mmol) and neat tetrabutylammonium fluoride (25 mL, 25 mmol). The reaction mixture was heated to 110° C. in an oil bath and allowed to stir for 2 h. The mixture was cooled and extracted with EtOAc and water, dried over MgSO4 and concentrate in vacuo. Purification by silica gel chromatography afforded 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylcyclopropyl)-benzo[d]thiazole. MS (ESI) m/z: Calculated: 431.1; Observed: 432.1 (M++1).

Workup

  1. customIn a reactor bottle were combined
  2. temperatureThe mixture was cooled
  3. extractionextracted with EtOAc and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrate in vacuo
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-2fb8c1998fa6480a8a3c0fccd8656784
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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