Potassium Acetate → 1-(7-Fluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinolin-4-yl)-3,3-dimethyl-2,3-dihydro-1h-pyrrolo[3,2-b]pyridin-6-ylboronic acid

HRID 1618547Notes

Reaction equation

HRID 1618547 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10]([C:11]3[C:20]4[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=4)[N:14]=[C:13]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[S:28]([CH3:31])(=[O:30])=[O:29])[C:12]=3[CH3:32])[CH2:9][C:8]([CH3:34])([CH3:33])[C:5]2=[N:6][CH:7]=1.[B:35]1(B2OC(C)(C)C(C)(C)O2)[O:39]C(C)(C)C(C)(C)[O:36]1.C([O-])(=O)C.[K+]>O1CCOCC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.[Pd]>[F:21][C:17]1[CH:16]=[C:15]2[C:20]([C:11]([N:10]3[C:4]4[C:5](=[N:6][CH:7]=[C:2]([B:35]([OH:39])[OH:36])[CH:3]=4)[C:8]([CH3:33])([CH3:34])[CH2:9]3)=[C:12]([CH3:32])[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[S:28]([CH3:31])(=[O:29])=[O:30])=[N:14]2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 67284726HCID 67284726, compound

Product 1

HCID 672852541-(7-Fluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinolin-4-yl)-3,3-dimethyl-2,3-dihydro-1h-pyrrolo[3,2-b]pyridin-6-ylboronic acid

Reagents, catalysts & solvents 2

HCID 2734559Bis(tricyclohexylphosphine) palladium(0)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A stirred solution of 4-(6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]-pyridin-1-yl)-7-fluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline (93 mg, 0.17 mmol) (described herein) in 1,4-dioxane (2.5 mL) was sparged with N2 for 10 min. After this time bis(pinacolato)diboron (48.1 mg, 0.19 mmol), potassium acetate (25.3 mg, 0.26 mmol), and bis(tricyclohexylphosphine)palladium(o) (11.5 mg, 0.017 mmol) were added and the reaction heated at 100° C. for 16 h. The reaction was cooled to rt and partitioned between EtOAc and water. The organic layer was dried (MgSO4) and concentrated, affording crude 1-(7-fluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinolin-4-yl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-ylboronic acid. No further purification was attempted. Mass Spectrum (ESI) m/e=506 (M+1).

Workup

  1. customwas sparged with N2 for 10 min
  2. temperatureThe reaction was cooled to rt
  3. custompartitioned between EtOAc and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5246e17273ed43438bfad15b453df4b0
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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