Dichloromethane → 4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanone

HRID 2095679Notes

Reaction equation

HRID 2095679 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([O:9][CH3:10])[C:3]=1[C@H:11]([C:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19]([C:22]3[CH:23]=[N:24][N:25]([C@@H:28]4[CH2:33][CH2:32][C@H:31]([OH:34])[CH2:30][CH2:29]4)[C:26]=3[CH3:27])[CH:20]=2)[NH:15][CH:14]=1)[CH3:12].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(Cl)Cl>>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([O:9][CH3:10])[C:3]=1[C@H:11]([C:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19]([C:22]3[CH:23]=[N:24][N:25]([CH:28]4[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]4)[C:26]=3[CH3:27])[CH:20]=2)[NH:15][CH:14]=1)[CH3:12]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 178491836HCID 178491836, compound

Product 1

HCID 546746704-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanone

Procedure

A solution of cis-4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanol (140.0 mg, 0.2899 mmol), Dess-Martin periodinane (184.4 mg, 0.4348 mmol) and DCM (10 mL, 200 mmol) was stirred at rt for 1 h. The material was extracted with DCM and sat. NaHCO3, and the organic layer was loaded onto silica gel for column chromatography, eluting with 2-4% MeOH/DCM. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a tan solid. MS (ES+): m/z=481.18/483.18 (100/50) [MH+]. HPLC: tR=1.49 min (polar—3 min, UPLC-ACQUITY).

Workup

  1. extractionThe material was extracted with DCM and sat. NaHCO3
  2. washeluting with 2-4% MeOH/DCM
  3. additionThe fractions containing the pure product
  4. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-5a160a587b0648aea1bed34e698380b9
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

Loading…