Sodium Hydroxide → 3-Fluoro-4-(5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

HRID 1177434ノート

反応式

HRID 1177434 の反応式
[O:1]1CCCO[CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([C:22]2([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[N:16]=3)=[C:9]([F:34])[CH:8]=1.[OH-].[Na+]>C1COCC1>[F:34][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[C:13]1[S:14][C:15]2[C:20]([N:21]=1)=[CH:19][CH:18]=[C:17]([C:22]1([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)[N:16]=2)[CH:2]=[O:1]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 671117162-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine

生成物 1

HCID 866387093-Fluoro-4-(5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

A slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine (0.467 g, 0.984 mmol) in 5 mL 1:1 THF/5N HCl was sealed and heated to 80° C. The resulting yellow solution was allowed to stir 3 h, was cooled, and then was treated with ice and 10N NaOH until basic. The reaction mixture was partitioned between EA and water, washed with water, brine, dried over sodium sulfate, filter, concentrate in vacuo to give 3-fluoro-4-(5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde as an oil/solid that contained some starting material. This material was carried on without further pyrification. MS (ESI) m/z: Calculated: 416.1; Observed: 417.1 (M++1).

後処理

  1. temperaturewas cooled
  2. customThe reaction mixture was partitioned between EA and water
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

出典と根拠

ORDレコード
ord-37faf0cc30e4438db0bb53091cb60d56
出典データセット
uspto-grants-2010_11
特許番号
US07842685B2

反応ノート

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