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 1618547노트

반응식

HRID 1618547 반응식
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

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 2

HCID 2734559Bis(tricyclohexylphosphine) palladium(0)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5246e17273ed43438bfad15b453df4b0
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765940B2

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