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

HRID 2095721Notes

Reaction equation

HRID 2095721 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([O:9][CH:10]([F:12])[F:11])[C:3]=1[C@H:13]([C:15]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([C:24]3[CH:25]=[N:26][N:27]([C@H:30]4[CH2:35][CH2:34][C@H:33]([OH:36])[CH2:32][CH2:31]4)[C:28]=3[CH3:29])[CH:22]=2)[NH:17][CH:16]=1)[CH3:14].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].C(Cl)Cl>>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([O:9][CH:10]([F:12])[F:11])[C:3]=1[C@H:13]([C:15]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([C:24]3[CH:25]=[N:26][N:27]([CH:30]4[CH2:35][CH2:34][C:33](=[O:36])[CH2:32][CH2:31]4)[C:28]=3[CH3:29])[CH:22]=2)[NH:17][CH:16]=1)[CH3:14]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 178422172HCID 178422172, compound

Product 1

HCID 546737614-[4-(3-{(1S)-1-[2-Chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]cyclohexanone

Procedure

A solution of trans-4-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]cyclohexanol (70.0 mg, 0.135 mmol), Dess-Martin periodinane (85.82 mg, 0.2023 mmol), NaHCO3 (22.66 mg, 0.2698 mmol) and DCM (4 mL, 70 mmol) was stirred at rt for 5 min. 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 white solid. MS (ES+): m/z=517.11/519.08 (100/50) [MH+]. HPLC: tR=3.99 min (polar—5 min, ZQ3).

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-f5f9dc95f8134409b9af6f6e6f1aca54
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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