Trifluoroacetic acid → HCID 59803827, compound

HRID 253478Notes

Reaction equation

HRID 253478 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH:17]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([Cl:28])[CH:26]=3)[NH:21][CH:20]=2)O)=[C:11]([F:29])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C(OC)=CC(C(OC)C2C3C(=NC=C(Cl)C=3)NC=2)=C(F)C=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH2:17][C:19]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([Cl:28])[CH:26]=3)[NH:21][CH:20]=2)=[C:11]([F:29])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 66889479HCID 66889479, compoundHCID 66890123HCID 66890123, compound

Product 1

HCID 59803827HCID 59803827, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(4-Benzyloxy-2-fluoro-5-methoxy-phenyl)-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol 223a and 3-[(4-benzyloxy-2-fluoro-5-methoxy-phenyl)-methoxy-methyl]-5-chloro-1H-pyrrolo[2,3-b]pyridine 223b (48 mmol) were combined with acetonitrile (1.4 L), trifluoroacetic acid (21 mL, 288 mmol) and triethylsilane (31 mL, 192 mmol). The resulting mixture was stirred for two hours at reflux. The solvent was removed under reduced pressure. Ethyl acetate (6 L) was added and the organic layer was washed with aqueous potassium carbonate saturated solution. The layers were separated and the aqueous layer was back-extracted with ethyl acetate (2 L). The combined organic portions were dried over anhydrous sodium sulfate and evaporated under reduced pressure to give the desired compound 224 which was used without further purification.

Workup

  1. temperatureat reflux
  2. customThe solvent was removed under reduced pressure
  3. additionEthyl acetate (6 L) was added
  4. washthe organic layer was washed with aqueous potassium carbonate saturated solution
  5. customThe layers were separated
  6. extractionthe aqueous layer was back-extracted with ethyl acetate (2 L)
  7. dry with materialThe combined organic portions were dried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c7f6605eb7654c87921d2dc59a311987
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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