Tetrahydrofuran → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(4-phenylhepta-1,6-dien-4-yl)thiazolo[5,4-b]pyridine

HRID 1177425ノート

反応式

HRID 1177425 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]([CH:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:23][CH:24]=[CH2:25])[N:16]=3)=[C:9]([F:32])[CH:8]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].O1C[CH2:46][CH2:45][CH2:44]1.C(I)C=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]([C:22]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([CH2:46][CH:45]=[CH2:44])[CH2:23][CH:24]=[CH2:25])[N:16]=3)=[C:9]([F:32])[CH:8]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 11166Allyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 686357552-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylbut-3-enyl)-thiazolo[5,4-b]pyridine

生成物 1

HCID 671121072-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(4-phenylhepta-1,6-dien-4-yl)thiazolo[5,4-b]pyridine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylbut-3-enyl)-thiazolo[5,4-b]pyridine (1.17 g, 2.62 mmol) in 20 mL DMF under argon was added sodium bis(trimethylsilyl)amide, 1.0M solution in tetrahydrofuran (3.28 mL, 3.28 mmol). The reaction mixture became deep blue/purple. After 2 min, allyl iodide (0.362 mL, 3.93 mmol) was added and the reaction became light orange after 1 min. After 5 min total, the reaction mixture was quenched with sat'd aq. NH4Cl, EtOAc, and water. The organic layer was washed with water, brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography, ISCO, 80 g, 0-40% EA/hexanes to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(4-phenylhepta-1,6-dien-4-yl)thiazolo[5,4-b]pyridine as a white foam. MS (ESI) m/z: Calculated: 486.2; Observed: 487.1 (M++1).

後処理

  1. waitthe reaction became light orange after 1 min
  2. waitAfter 5 min total
  3. customthe reaction mixture was quenched with sat'd aq. NH4Cl, EtOAc, and water
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography, ISCO, 80 g, 0-40% EA/hexanes

出典と根拠

ORDレコード
ord-ffae73a642c44e17bf4212e1fe0366dd
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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