Diethyl Ether → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-phenyl-2-(trimethylsilyl)cyclopropyl)benzo[d]thiazole

HRID 1177443Notes

Reaction equation

[CH3:1][Si:2]([CH:5]=[N+]=[N-])([CH3:4])[CH3:3].C(OCC)C.[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][CH:37]=4)=[CH2:35])[CH:31]=[CH:30][C:28]=3[N:29]=2)=[C:21]([F:42])[CH:20]=1>O1CCOCC1>[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:37]=[CH:38][CH:39]=[CH:40][CH:41]=5)[CH2:35][CH:5]4[Si:2]([CH3:1])([CH3:3])[CH3:4])[CH:31]=[CH:30][C:28]=3[N:29]=2)=[C:21]([F:42])[CH:20]=1

Participants

Conditions

Temperature: 150 °C

Procedure

In a reactor bottle (trimethylsilyl)diazomethane, 2.0 M in diethyl ether (2.4 mL, 4.8 mmol) was added to a mixture of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylvinyl)-benzo[d]thiazole (0.650 g, 1.6 mmol), in anhydrous dioxane 15.00 mL. The reaction mixture was heated to 150° C. for 18 h. At which time the crude reaction mixture was concentrate in vacuo and purified by silica gel chromatography to afford as a mixture of isomers 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-phenyl-2 (trimethylsilyl)cyclopropyl)benzo[d]thiazole. MS (ESI) m/z: Calculated: 503.2; Observed: 504.0 (M++1).

Workup

customAt which time the crude reaction mixture
concentrationwas concentrate in vacuo
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-a1afe318cb5b4a81a5e6bbdc5dbf16fc
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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