Reaction SMILES: [CH3:1][C:2]1([CH3:30])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]3[N:28]=[C:15]4[CH:16]=[CH:17][CH:18]=[C:19]([C:20]([CH:22]5[CH2:27][CH2:26][O:25][CH2:24][CH2:23]5)=[CH2:21])[N:14]4[N:13]=3)=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:29].C[Si](C[Mg]Cl)(C)C.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C.O>[CH3:30][C:2]1([CH3:1])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]3[N:28]=[C:15]4[CH:16]=[CH:17][CH:18]=[C:19]([CH:20]([CH:22]5[CH2:27][CH2:26][O:25][CH2:24][CH2:23]5)[CH3:21])[N:14]4[N:13]=3)=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:29]
Reactant: C=C(c1cccc2nc(Nc3ccc4c(c3)NC(=O)C4(C)C)nn12)C1CCOCC1
Agent: C[Si](C)(C)C[Mg]Cl
Agent: [Cl-]
Agent: [NH4+]
Solvent: O
Solvent: C1CCOC1
Solvent: CCOC(C)=O
Product: CC(c1cccc2nc(Nc3ccc4c(c3)NC(=O)C4(C)C)nn12)C1CCOCC1
Temperature: 0 °C
Yield: 64 %

Procedure:
3,3-Dimethyl-6-(5-(1-(tetrahydro-2H-pyran-4-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)indolin-2-one. (Trimethylsilylmethyl)-magnesium chloride (0.700 mL, 0.700 mmol, 1 M in diethyl ether) was added dropwise slowly to a stirred solution of tert-butyl 3,3-dimethyl-2-oxo-6-(5-(tetrahydro-2H-pyran-4-carbonyl)-[1,2,4]triazolo[1,5-c]pyridin-2-ylamino)indoline-1-carboxylate (0.118 g, 0.233 mmol) in tetrahydrofuran (10 mL) at −70° C. under nitrogen. The reaction mixture became dark red-colored upon addition of the Grignard reagent. The resulting mixture was stirred under nitrogen while slowly warming to 0° C. over 2 h. More (trimethylsilylmethyl)-magnesium chloride (0.233 mL, 0.233 mmol, 1 M in diethyl ether) was added and the resulting red solution was stirred at 0° C. under nitrogen for 35 min. More (trimethylsilylmethyl)-magnesium chloride (0.350 mL, 0.350 mmol, 1 M in diethyl ether) was added and the resulting mixture was stirred at 0° C. under nitrogen for 1.5 h. More (trimethylsilylmethyl)-magnesium chloride (0.350 mL, 0.350 mmol, 1 M in diethyl ether) was added and the resulting mixture was stirred at 0° C. under nitrogen for 1 h. Saturated aqueous ammonium chloride was added to quench the reaction. The resulting mixture was diluted with ethyl acetate and water and shaken in a separatory funnel. The layers were separated and the organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated on a rotary evaporator. The residue was taken up in dichloromethane and purified using flash chromatography (Biotage) (20-100% ethyl acetate in hexane) to an impure white solid. MS (ESI) m/z 594.5 [M+H]+. To the white solids was added acetic acid (5 mL). The resulting mixture was stirred and heated at 120° C. under a reflux condenser for 85 h. The resulting mixture was filtered and purified using reverse-phase preparatory HPLC (10-60% acetonitrile+0.1% trifluoroacetic acid in water+0.1% trifluoroacetic acid, over 30 min). Fractions containing the desired product were loaded onto a Strata X—C ion exchange column from Phenomenex. The column was washed successively with water, acetonitrile, methanol, and then a mixture of 5% ammonium hydroxide, 45% methanol, and 50% dichloromethane. The product came off with the ammonium hydroxide eluent and was concentrated on a rotary evaporator and dried under high vacuum to give the desired product (0.035 g, 0.087 mmol, 64% yield) as an off-white solid. MS (ESI) m/z 404.5 [M+1]+.