[NH:1]1[CH2:4][CH:3]([CH2:5][N:6]2[C:14]3[C:9](=[CH:10][C:11]([O:15][CH:16]([F:18])[F:17])=[CH:12][CH:13]=3)[C:8]([C:19]3[N:20]=[C:21]4[C:27]([C:28]([NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:26][N:25]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[C:22]4=[N:23][CH:24]=3)=[N:7]2)[CH2:2]1.C=O.[C:45](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[C:31]([NH:30][C:28]([C:27]1[C:21]2[C:22](=[N:23][CH:24]=[C:19]([C:8]3[C:9]4[C:14](=[CH:13][CH:12]=[C:11]([O:15][CH:16]([F:18])[F:17])[CH:10]=4)[N:6]([CH2:5][CH:3]4[CH2:4][N:1]([CH3:45])[CH2:2]4)[N:7]=3)[N:20]=2)[N:25]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[CH:26]=1)=[O:29])([CH3:33])([CH3:34])[CH3:32]To a stirred solution of 2-(1-(azetidin-3-ylmethyl)-5-(difluoromethoxy)-1H-indazol-3-yl)-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (37 mg, 61.7 μmol) in methanol (4 mL), cooled to 0° C. with ice bath, was added aqueous formaldehyde (1 mL, 13.4 mmol), followed by the addition of sodium triacetoxyborohydride (29.4 mg, 139 μmol). The reaction mixture was stirred at room temperature for 15 h then concentrated and purified by chromatography (silica, 4 g Analogix column, 0-10% methanol containing 10% ammonium hydroxide in dichloromethane) to give N-tert-butyl-2-(5-(difluoromethoxy)-1-((1-methylazetidin-3-yl)methyl)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (33 mg, 87%). MS (M+H)+=614.
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