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

HRID 1177434노트

반응식

HRID 1177434 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-37faf0cc30e4438db0bb53091cb60d56
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842685B2

반응 노트

불러오는 중…