Cesium fluoride → HCID 67111508, compound

HRID 1177492Notes

Reaction equation

HRID 1177492 reaction equation
[F-].[Cs+].FC(F)(F)S(O[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])=[CH2:10])(=O)=O.[F:20][C:21]1[CH:22]=[C:23]([CH2:40][N:41]2[CH2:44][CH:43]([C:45]([O:47][CH3:48])=[O:46])[CH2:42]2)[CH:24]=[CH:25][C:26]=1[C:27]1[S:28][C:29]2[C:34]([N:35]=1)=[CH:33][CH:32]=[C:31]([Sn](C)(C)C)[N:30]=2>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:20][C:21]1[CH:22]=[C:23]([CH2:40][N:41]2[CH2:42][CH:43]([C:45]([O:47][CH3:48])=[O:46])[CH2:44]2)[CH:24]=[CH:25][C:26]=1[C:27]1[S:28][C:29]2[C:34]([N:35]=1)=[CH:33][CH:32]=[C:31]([C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])=[CH2:10])[N:30]=2

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 59174917HCID 59174917, compoundHCID 86638714HCID 86638714, compound

Product 1

HCID 67111508HCID 67111508, compound

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
45 °C

Procedure

A sealable tube was charged with Cu(I) iodide (7.32 mg, 0.0384 mmol), cesium fluoride (0.117 g, 0.769 mmol), 1-(2-fluorophenyl)vinyl trifluoromethane-sulfonate (0.208 g, 0.769 mmol), tetrakis(triphenylphosphine) palladium (0) (0.0222 g, 0.0192 mmol), methyl 1-((3-fluoro-4-(5-(trimethylstannyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate (0.200 g, 0.384 mmol), flushed with argon, diluted with 0.8 mL DMF, sealed, and heated to 45° C. overnight. The reaction mixture was partitioned between EA, water, saturated sodium bicarbonate. The organic layer was washed with water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by silica gel chromatography, 12 g, 0-100% EA/hexanes provided methyl 1-((3-fluoro-4-(5-(1-(2-fluorophenyl)vinyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate as an oil which slowly solidified to a tan solid. MS (ESI) m/z: calculated: 477.1; Observed: 478.1 (M++1).

Workup

  1. customflushed with argon
  2. additiondiluted with 0.8 mL DMF
  3. customsealed
  4. customThe reaction mixture was partitioned between EA, water, saturated sodium bicarbonate
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by silica gel chromatography, 12 g, 0-100% EA/hexanes

Sources & evidence

ORD record
ord-3d5a929c046d4db09d49cb79245a7d21
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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