Potassium Carbonate → [2,6-dichloro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo-[2,3-b]pyridin-3-yl]-methanone

HRID 253436Notes

Reaction equation

HRID 253436 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=[C:4]([Cl:14])[C:3]=1[CH:15]([C:17]1[C:25]2[C:20](=[N:21][CH:22]=[C:23]([C:26]3[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=3)[CH:24]=2)[NH:19][CH:18]=1)[OH:16].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]([F:13])([F:11])[F:12])=[CH:6][CH:5]=[C:4]([Cl:14])[C:3]=1[C:15]([C:17]1[C:25]2[C:20](=[N:21][CH:22]=[C:23]([C:26]3[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=3)[CH:24]=2)[NH:19][CH:18]=1)=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 159087TriacetoxyperiodinaneHCID 59803863[2,6-dichloro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methanol

Product 1

HCID 24954128[2,6-dichloro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo-[2,3-b]pyridin-3-yl]-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To [2,6-dichloro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methanol (116, 100.0 mg, 0.21 mmol) in dichloromethane (10.0 mL), Dess-Martin periodinane (108 mg, 0.26 mmol) was added. The reaction was stirred at room temperature for 10 minutes. The reaction mixture was poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give a white solid (P-2151, 19.4 mg, 19.5%). MS (ESI) [M+H+]+=469.1.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 20% to 100% ethyl acetate in hexane
  7. customto give a white solid (P-2151, 19.4 mg, 19.5%)

Sources & evidence

ORD record
ord-06c558b358f746c7b3ba118c9c89f7c5
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

Loading…