Trifluoroacetic acid → HCID 59683323, compound

HRID 2206572Notes

Reaction equation

HRID 2206572 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([CH2:9]O)[NH:8][C:4]=2[N:3]=[CH:2]1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:9][C:7]1[NH:8][C:4]2[N:3]=[CH:2][S:1][C:5]=2[CH:6]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 673667544H-Pyrrolo[2,3-d]thiazole-5-methanol

Product 1

HCID 59683323HCID 59683323, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4H-pyrrolo[2,3-d]thiazol-5-yl)methanol (3.5 g, 22.7 mmol) in anhydrous dichloromethane (50 mL) was added triethylsilane (5.23 g, 45.4 mmol) dropwise below 0° C., trifluoroacetic acid (5.18 g, 45.4 mmol) was added dropwise followed below 0° C. The resulting reaction system was warm to the ambient temperature and allowed to stir for 2 hours at room temperature. The reaction mixture was poured into saturated sodium bicarbonate, extracted with dichloromethane (50 mL×3), the combined organic phase was dried by anhydrous sodium sulphate, and then filtered. The filtrate was concentrated and purified by column chromatograph on silica gel eluted with (petrol ether/acetic ester 15:1→8:1) to give the title compound (2.5 g, 80%) as a yellow solid. LCMS (M+H+) m/z: calc'd. 138.03. found 138.9.

Workup

  1. additionwas added dropwise followed below 0° C
  2. customThe resulting reaction system
  3. extractionextracted with dichloromethane (50 mL×3)
  4. dry with materialthe combined organic phase was dried by anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by column chromatograph on silica gel
  8. washeluted with (petrol ether/acetic ester 15:1→8:1)

Sources & evidence

ORD record
ord-8665dc5383564aa3a1a88735cfe42c6e
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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