Triacetoxyperiodinane → HCID 67111563, compound

HRID 1177486Notes

Reaction equation

HRID 1177486 reaction equation
[F:1][C:2]([F:31])([F:30])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][C:13]3[C:18]([N:19]=2)=[CH:17][CH:16]=[C:15]([C:20]2([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:22][CH2:21]2)[N:14]=3)=[C:7]([F:29])[CH:6]=1)[OH:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOC(C)=O.CCCCCC>C(Cl)Cl>[F:31][C:2]([F:1])([F:30])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][C:13]3[C:18]([N:19]=2)=[CH:17][CH:16]=[C:15]([C:20]2([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:21][CH2:22]2)[N:14]=3)=[C:7]([F:29])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 21226206Ethyl acetate hexaneHCID 67111469HCID 67111469, compound

Product 1

HCID 67111563HCID 67111563, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,2,2-trifluoro-1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo-[5,4-b]pyridine-2-yl)phenyl)ethanol (1.15 g, 2.6 mmol) in 25 mL DCM under nitrogen was added Dess-Martin Periodinane (2.0 g, 4.7 mmol) in one portion. The reaction mixture was allowed to stir for 3 h. The reaction mixture was quenched with sat'd aq. Sodium thiosulfate (2 mL) and 25 mL sat'd aq. Sodium bicarbonate and allowed to stir rapidly for 30 min. The organic layer was separated and the aq. Layer was extracted with DCM, combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to give a yellow foam. The material was treated with DCM and passed through a Redi-Sep® pre-packed silica gel column (40 g) using 0-60% EtOAc/hexane. The product-containing fractions were concentrated to afford 2,2,2-trifluoro-1-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)ethanone as a yellowish foam. The foam was treated with hexanes and concentrated in vacuo a few times to give a nice light yellow solid. MS (ESI) m/z: calculated: 442.1; Observed: 461.0 (M++H2O+1).

Workup

  1. customThe reaction mixture was quenched with sat'd aq. Sodium thiosulfate (2 mL) and 25 mL
  2. stirringto stir rapidly for 30 min
  3. customThe organic layer was separated
  4. extractionthe aq. Layer was extracted with DCM
  5. dry with materialcombined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a yellow foam
  9. concentrationThe product-containing fractions were concentrated

Sources & evidence

ORD record
ord-33852990805b41828dbdf0a01976c6f1
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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