(2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazol-6-yl)(pyridine-2-yl)methanone → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-(pyridin-2-yl)vinyl)benzo[d]thiazole

HRID 1177554Notes

Reaction equation

[CH2:1]([Li])CCC.[O:6]1[CH2:11][CH2:10][CH2:9][O:8][CH:7]1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:19][C:20]3[CH:26]=[C:25]([C:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)=O)[CH:24]=[CH:23][C:21]=3[N:22]=2)=[C:14]([F:35])[CH:13]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[O:8]1[CH2:9][CH2:10][CH2:11][O:6][CH:7]1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:19][C:20]3[CH:26]=[C:25]([C:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)=[CH2:1])[CH:24]=[CH:23][C:21]=3[N:22]=2)=[C:14]([F:35])[CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

n-Butyllithium (2.5 M in hexanes, 1.80 mL, 4.50 mmol) was added to a suspension of methyltriphenylphosphonium bromide (1.78 g, 5.00 mmol) in THF (10 mL) at −78° C. and the mixture was warmed to 0° C. over 30 min. The suspension (1 mL, about 3 equiv Wittig reagent) was added to a suspension of (2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-benzo[d]thiazol-6-yl)(pyridine-2-yl)methanone (0.09 g, 0.21 mmol) in THF (1 mL) and the mixture was stirred for 16 h at RT. The solvent was remove under vacuum and the resulting oil was purified by silica gel chromatography to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-(pyridin-2-yl)vinyl)benzo[d]thiazole as a white solid. MS (ESI) m/z: Calculated: 418.1; Observed: 419.1 (M++1).

Workup

customThe solvent was remove under vacuum
customthe resulting oil was purified by silica gel chromatography

Sources & evidence

ORD record: ord-fba0258e0a2d40cd8883e99f57dcbe1e
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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