Water → HCID 178472397, compound

HRID 2095643Notes

Reaction equation

HRID 2095643 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C@@H:11]([C:13]3[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]([F:21])[C:14]=3[Cl:22])[CH3:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:23][C:24]1[N:28]([C@H:29]2[CH2:34][CH2:33][C@H:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:31][CH2:30]2)[N:27]=[CH:26][C:25]=1B1OC(C)(C)C(C)(C)O1.[F-].[K+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[Cl:22][C:14]1[C:15]([F:21])=[CH:16][CH:17]=[C:18]([O:19][CH3:20])[C:13]=1[C@H:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:25]3[CH:26]=[N:27][N:28]([C@H:29]4[CH2:30][CH2:31][C@H:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:33][CH2:34]4)[C:24]=3[CH3:23])[CH:3]=2)[NH:8][CH:9]=1)[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 522689Potassium FluorideHCID 670045375-Bromo-3-[(S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridineHCID 178472396HCID 178472396, compound

Product 1

HCID 178472397HCID 178472397, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-bromo-3-[(S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (57.8 mg, 0.150 mmol), ethyl trans-4-[5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]cyclohexanecarboxylate (60.0 mg, 0.166 mmol), Pd(PPh3)4 (8.70 mg, 0.00753 mmol), potassium fluoride (26.2 mg, 0.452 mmol) and 4:1 dioxane:H2O (3 mL, 30 mmol) was heated to 90° C. for 2 h. The organic solvent was removed in vacuo, and the material was extracted with DCM and water. The organic layer was purified via column chromatography, eluting with 1-3% 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=539.16/541.16 (100/50) [MH+]. HPLC: tR=3.98 min (polar—5 min, ZQ3).

Workup

  1. customThe organic solvent was removed in vacuo
  2. extractionthe material was extracted with DCM and water
  3. customThe organic layer was purified via column chromatography
  4. washeluting with 1-3% MeOH/DCM
  5. additionThe fractions containing the pure product
  6. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-92f3dce6ae464cddbc093bb500252ca9
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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