Trifluoroacetic acid → HCID 52933299, compound

HRID 510016Notes

Reaction equation

HRID 510016 reaction equation
C(OC(=O)[N:7]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[Cl:45])[C:8]1[CH:13]=[CH:12][C:11]([CH:14](O)[C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]([Si](C(C)C)(C(C)C)C(C)C)[CH:16]=2)=[C:10]([F:37])[N:9]=1)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:45][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[CH2:38][NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([O:24][CH3:25])[CH:22]=3)[NH:17][CH:16]=2)=[C:10]([F:37])[N:9]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 58258914HCID 58258914, compound

Product 1

HCID 52933299HCID 52933299, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (2-chloro-benzyl)-{6-fluoro-5-[hydroxy-(5-methoxy-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-pyridin-2-yl}-carbamic acid tert-butyl ester (176, 400 mg, 0.598 mmol) in 20.0 mL of dichloromethane, triethylsilane (2.00 mL, 12.5 mmol) and trifluoroacetic acid (1.00 mL, 13.0 mmol) were added. The reaction was stirred at room temperature for 4 hours, then poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 20-100% ethyl acetate in hexane. Appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound as a white solid (P-2034, 60.7 mg). MS (ESI) [M+H+]+=397.1.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material was purified by silica gel column chromatography
  6. washeluting with 20-100% ethyl acetate in hexane
  7. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-6f99c6d147194aebbef1bcbf38af2ce5
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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