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

HRID 1177424Notes

Reaction equation

HRID 1177424 reaction equation
[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.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].O1C[CH2:43][CH2:42][CH2:41]1.C(I)C=C.[NH4+].[Cl-]>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)[CH2:43][CH:42]=[CH2:41])[N:16]=3)=[C:9]([F:29])[CH:8]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 11166Allyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 591748722-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-benzylthiazolo[5,4-b]pyridine

Product 1

HCID 686357552-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylbut-3-enyl)-thiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-benzylthiazolo[5,4-b]pyridine (2.28 g, 5.6 mmol) in 40 mL DMF under argon was added lithium bis(trimethylsilyl)amide, 1.0 m solution in tetrahydrofuran (7.0 mL, 7.0 mmol). A very deep blue solution resulted. After 2 min, allyl iodide (0.77 mL, 8.4 mmol) was added via syringe and the reaction became brown. After 5 min, sat'd aq. NH4Cl was added and the reaction partitioned between water and EA. The organic was washed with water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting material was sonicated in MTBE, filtered, and dried to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylbut-3-enyl)thiazolo[5,4-b]pyridine as a yellow solid. MS (ESI) m/z: Calculated: 446.2; Observed: 447.1 (M++1).

Workup

  1. customA very deep blue solution resulted
  2. waitAfter 5 min
  3. additionwas added
  4. customthe reaction partitioned between water and EA
  5. washThe organic was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting material was sonicated in MTBE
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-32fbbe606ad4433d9cc4f10c0db43dee
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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