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

HRID 1618514Notes

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][N:23]=4)[C:12]=3[CH3:28])[CH2:9][C:8]([CH3:30])([CH3:29])[C:5]2=[N:6][CH:7]=1.[B:31]1(B2OC(C)(C)C(C)(C)O2)[O:35]C(C)(C)C(C)(C)[O:32]1.C([O-])(=O)C.[K+]>O1CCOCC1>[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:31]([OH:35])[OH:32])[CH:3]=4)[C:8]([CH3:29])([CH3:30])[CH2:9]3)=[C:12]([CH3:28])[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[N:14]2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Prepared according to procedure O using 4-(6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (100 mg, 0.22 mmol), Pd(PCy3)2 (14.4 mg, 0.022 mmol), bis(pinacolato)diboron (60 mg, 0.24 mmol) and potassium acetate (35 mg, 0.32 mmol) in 1,4-dioxane (4.0 mL) and heating at 120° C. in the microwave for 1 h. After aqueous work up 1-(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-ylboronic acid was obtained as a colorless film. Mass Spectrum (ESI) m/e=429 (M+1).

Workup

customPrepared

Sources & evidence

ORD record: ord-e5322139d1984a8da18c4e3ca57f6be0
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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