Tetrahydrofuran → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylpent-4-enyl)thiazolo[5,4-b]pyridine

HRID 1177430ノート

反応式

HRID 1177430 の反応式
[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[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:16]=3)=[C:9]([F:29])[CH:8]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:40]1[CH2:44]O[CH2:42][CH2:41]1.BrCCC=C>CN(C=O)C>[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[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([CH:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:42][CH2:41][CH:40]=[CH2:44])[N:16]=3)=[C:9]([F:29])[CH:8]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 21241Homoallyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 591748722-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-benzylthiazolo[5,4-b]pyridine

生成物 1

HCID 686359872-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylpent-4-enyl)thiazolo[5,4-b]pyridine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Argon was bubbled through a slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-benzylthiazolo[5,4-b]pyridine (1.00 g, 2.46 mmol) in 20 mL DMF for 5 min. To the rapidly stirring reaction mixture was added LiHMDS 1.0M in THF (2.71 mL, 2.71 mmol) rapidly dropwise. The resulting deep blue reaction mixture was stirred for 2 min, at which point 4-bromo-1-butene (0.499 mL, 4.92 mmol) was added rapidly via syringe. The color of the reaction slowly became purple over 5 min, then brown over about 10-15 min additional. After 1.5 h, the reaction mixture was quenched with sat'd aq. NH4Cl and MTBE. The organic layer was washed with water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylpent-4-enyl)thiazolo[5,4-b]pyridine as an orange solid MS (ESI) m/z: Calculated: 460.2; Observed: 461.1 (M++1).

後処理

  1. customreaction mixture
  2. customThe resulting deep blue reaction mixture
  3. additionwas added rapidly via syringe
  4. customThe color of the reaction slowly became purple over 5 min
  5. waitAfter 1.5 h
  6. customthe reaction mixture was quenched with sat'd aq. NH4Cl and MTBE
  7. washThe organic layer was washed with water, brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8130528c5699496f8d40d868437c87fb
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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