Reaction SMILES: Br[C:2]1[CH:3]=[C:4]2[C:10]([C@@H:11]([C:13]3[C:18]([O:19][CH2:20][C@@H:21]4[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22]4)=[CH:17][CH:16]=[C:15]([F:28])[C:14]=3[Cl:29])[CH3:12])=[CH:9][N:8]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:5]2=[N:6][CH:7]=1.[CH3:37][N:38]1[C:42]([CH3:43])=[C:41](B(O)O)[CH:40]=[N:39]1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:29][C:14]1[C:15]([F:28])=[CH:16][CH:17]=[C:18]([O:19][CH2:20][C@@H:21]2[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22]2)[C:13]=1[C@H:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:41]3[CH:40]=[N:39][N:38]([CH3:37])[C:42]=3[CH3:43])[CH:3]=2)[N:8]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:9]=1)[CH3:12]
Reactant: C[C@H](c1c(OC[C@@H]2COC(C)(C)O2)ccc(F)c1Cl)c1cn(C(=O)OC(C)(C)C)c2ncc(Br)cc12
Reactant: Cc1c(B(O)O)cnn1C
Agent: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: O=C([O-])[O-]
Agent: [K+]
Solvent: O
Solvent: C1COCCO1
Product: Cc1c(-c2cnc3c(c2)c([C@H](C)c2c(OC[C@@H]4COC(C)(C)O4)ccc(F)c2Cl)cn3C(=O)OC(C)(C)C)cnn1C
Temperature: 95 °C

Procedure:
A suspension of tert-butyl 5-bromo-3-[(1S)-1-(2-chloro-6-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (29.2 mg, 0.0500 mmol), 1,5-dimethyl-1H-pyrazole-4-boronic acid, pinacol ester (20.7 mg, 0.0885 mmol), Pd(PPh3)4 (2.8 mg, 0.0024 mmol), and potassium carbonate (33.2 mg, 0.240 mmol) in a 4:1 mixture of 1,4-dioxane (2 mL) to H2O (0.5 mL) was subjected to microwave heating [Biotage, 95° C.] for 20 min. The reaction was again subjected to microwave heating for an additional 20 minutes, which resulted in protected intermediate, tert-butyl 3-[(1S)-1-(2-chloro-6-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-3-fluorophenyl)ethyl]-5-(1,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate. The microwave vial was opened, 4.0 M of HCl in 1,4-dioxane (1 mL, 4 mmol) was added to the stirring suspension, and the reaction was stirred at rt for 1 h, which lead to the BOC-protected intermediate, tert-butyl 3-[(1S)-1-(2-chloro-6-{[(2S)-2,3-dihydroxypropyl]oxy}-3-fluorophenyl)ethyl]-5-(1,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate. 37% HCl (1 mL, 10 mmol) was added and stirred for 1 h at rt. Additional 37% HCl (1 mL, 10 mmol) was added and the reaction was stirred at rt for 15 h. The reaction mixture was concentrated in vacuo. The sample was dissolved in a mixture of CH2Cl2 and MeOH, passed through a syringe filter to remove excess K2CO3, and concentrated in vacuo. The crude was adsorbed onto a pre-filled silica loading cartridge [RediSepRf, 5 gram] and purified using the Teledyne/ISCO purification system [RediSepRf 4 gram silica], eluting with a solvent gradient of 0-20% 7N NH3(MeOH):EtOAc. Fractions containing product were combined and concentrated in vacuo. The sample was dissolved in MeOH, syringe filtered, and purified a second time using MDP, under acidic conditions (TFA). Fractions containing product were combined and concentrated in vacuo. The sample was dissolved in minimal MeOH, syringe filtered, and purified a third time using HPLC, under acidic conditions (formic acid). Fractions containing product were combined and concentrated in vacuo, yielding the title material as a clear and colorless film. 1H NMR (400 MHz, CD3OD): δ=8.10 (br s, 1H), 7.44 (s, 1H), 7.39 (d, J=1.3 Hz, 1H), 7.36 (d, J=1.8 Hz, 1H), 7.08 (dd, J=8.8 Hz, 1H), 6.90 (dd, J=8.7, 4.2 Hz, 1H), 5.12 (br d, J=6.6 Hz, 1H), 3.83-3.90 (m, 1H), 3.81 (s, 3H), 3.76-3.80 (m, 1H), 3.70 (br s, 1H), 3.42-3.51 (m, 1H), 3.34-3.42 (m, 1H), 2.18 (s, 3H), 1.83 (d, J=7.1 Hz, 3H). MS (ES+): m/z 459.08/461.03 (100/74) [MH+]. HPLC: tR=2.93 min (ZQ3, polar—5 min).