Reaction SMILES: Cl.Cl.[F:3][C:4]1[C:12]([C:13]2[C:21]3[C:20]([NH2:22])=[N:19][CH:18]=[N:17][C:16]=3[N:15]([CH3:23])[CH:14]=2)=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][NH:8]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:57][C:58]1[CH:62]=[C:61]([CH3:63])[N:60]([CH2:64][C:65](O)=[O:66])[N:59]=1>CN(C=O)C.CO.C(Cl)Cl>[CH3:57][C:58]1[CH:62]=[C:61]([CH3:63])[N:60]([CH2:64][C:65]([N:8]2[C:9]3[C:5](=[C:4]([F:3])[C:12]([C:13]4[C:21]5[C:20]([NH2:22])=[N:19][CH:18]=[N:17][C:16]=5[N:15]([CH3:23])[CH:14]=4)=[CH:11][CH:10]=3)[CH2:6][CH2:7]2)=[O:66])[N:59]=1
Reactant: Cn1cc(-c2ccc3c(c2F)CCN3)c2c(N)ncnc21
Reactant: Cc1cc(C)n(CC(=O)O)n1
Agent: CN(C)C(On1nnc2cccnc21)=[N+](C)C
Agent: Cl
Agent: F[P-](F)(F)(F)(F)F
Solvent: CN(C)C=O
Solvent: CCN(C(C)C)C(C)C
Solvent: ClCCl
Product: Cc1cc(C)n(CC(=O)N2CCc3c2ccc(-c2cn(C)c4ncnc(N)c24)c3F)n1
Temperature: 0 °C
Reaction time: 0.5 h
Yield: 41.7 %

Procedure:
To a suspension of 5-(4-fluoro-2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine dihydrochloride (200 mg, 0.56 mmol, 1 equiv) and HATU (235 mg, 0.62 mmol, 1.1 equiv) in DMF (2 mL) at room temperature was added DIEA (314 uL, 1.80 mmol, 3.2 equiv) in one portion. To this mixture was added (3,5-dimethyl-1H-pyrazol-1-yl)acetic acid (87 mg, 0.56 mmol, 1 equiv) portionwise over a 1 h period. After another 30 min, LCMS showed there was still 27% starting amine left. To the mixture was added 18 mg of (3,5-dimethyl-1H-pyrazol-1-yl)acetic acid. After 1 hour, the mixture was poured into 20 mL of ice cold water to give a suspension, which was filtered. The cake was washed with water and dried under house vacuum to afford crude product, which was dissolved in 10% MeOH in DCM and absorbed onto a dryload cartridge. Purification was done on an Analogix SF25-40 g silica gel cartridge using gradient elution of 1% A in CHCl3 to 65% A in CHCl3 (A was a mixture of 3200/800/80 CHCl3/MeOH/NH4OH, gradient: 0-5 min: 1% A, 5-35 min 5-60% A). There were close-running (front running) impurities with slightly shorter retention time. The desired product eluted from 29-35% A. The combined fractions were concentrated in vacuo. The residue was dissolved in 10% MeOH in DCM and absorbed onto a dryload cartridge. Purification was done on an Analogix SF25-60 g silica gel cartridge using gradient elution of 1% A in EtOAc 100% A (A was a mixture of 20% MeOH in EtOAc). The desired product eluted from 90-100% A. Again, there was a non-polar impurity with slightly shorter retention time. The combined fractions were concentrated in vacuo. The residue was dissolved in 12 mL of 10% MeOH in DCM and concentrated in vacuo. The wet residue was diluted with 12 mL of MTBE. The resulting suspension was concentrated in vacuo to reduce to half volume. The mixture was diluted with another 6 mL of MTBE. The suspension was filtered. The cake was washed with MTBE (2×4 mL) and hexane (3×4 mL), and dried under vacuum at 65° C. for 18 h to afford 5-{1-[(3,5-dimethyl-1H-pyrazol-1-yl)acetyl]-4-fluoro-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (98 mg) as white solids. LC-MS (ES) m/z=420 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.10 (s, 3H), 2.16 (s, 3H), 3.29 (t, J=8.3 Hz, 2H), 3.74 (s, 3H), 4.34 (t, J=8.3 Hz, 2H), 5.11 (s, 2H), 5.86 (s, 1H), 5.93-6.17 (br s, 1.5H), 7.21 (t, J=8.1 Hz, 1H), 7.28 (s, 1H), 7.87 (d, J=8.1 Hz, 1H), 8.14 (s, 1H).