Triisopropyl borate → HCID 66731039, 화합물

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[CH:1]1([N:5]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([CH3:14])[CH:12]=3)[C:7]([C:16]#[N:17])=[CH:6]2)[CH2:4][CH2:3][CH2:2]1.[B:18](OC(C)C)([O:23]C(C)C)[O:19]C(C)C.[Li+].CC([N-]C(C)C)C>C1COCC1>[C:16]([C:7]1[C:8]2[C:13](=[CH:12][C:11]([CH3:14])=[C:10]([F:15])[CH:9]=2)[N:5]([CH:1]2[CH2:2][CH2:3][CH2:4]2)[C:6]=1[B:18]([OH:23])[OH:19])#[N:17]

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온도: -78 °C

실험 절차

Into a solution of 1-cyclobutyl-5-fluoro-6-methyl-1H-indole-3-carbonitrile (1.2 g, 5.3 mmol) and triisopropyl borate (2.18 mL, 9.47 mmol) in THF (20 mL) at −78° C. was added LDA (1.5 M in cyclohexane, 4.6 mL, 6.84 mmol). The mixture was stirred at −78° C. for 30 min and quenched with ice water (60 mL) and stirred for 15 min without cooling. The mixture was extracted with ethyl acetate 1:1 in hexane (20 mL). The aqueous layer was acidified with 2 N aq. HCl to pH 5 and then extracted with CH2Cl2 (60 mL). The organic layer was dried over Na2SO4 and concentrated to give 3-cyano-1-cyclobutyl-5-fluoro-6-methyl-1H-indol-2-ylboronic acid as a solid (1.44 g, 98% pure by LCMS) that was used in the next step without further purification.