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 1618547ノート

反応式

HRID 1618547 の反応式
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

参加物

6

反応物 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 672847264-(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

生成物 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

試薬・触媒・溶媒 2

HCID 2734559Bis(tricyclohexylphosphine) palladium(0)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5246e17273ed43438bfad15b453df4b0
出典データセット
uspto-grants-2014_07
特許番号
US08765940B2

反応ノート

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