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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1909959Generated: November 1, 2026

Benzeneacetic acid, 2-fluoro- → 5-{1-[(2-fluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

https://huagongshe.com/reaction/1909959

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzeneacetic acid, 2-fluoro-HCID 67979—
ReactantDiisopropylethylamineHCID 81531—
ReactantMethanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9886157—
Reactant5-(2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine dihydrochlorideHCID 66823470—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product5-{1-[(2-fluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amineHCID 5346782487%

Reaction Steps

In a 20 mL vial with cap, to the solution of 5-(2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine-2HCl (70.6 mg, 0.209 mmol), (2-fluorophenyl)acetic acid (32.2 mg, 0.209 mmol), HATU (79 mg, 0.209 mmol) in DMF (2 mL) was added Hunig's base (0.146 mL, 0.836 mmol). The mixture was stirred at room temperature for overnight. LCMS showed reaction was completed. The reaction was poured into water, white solid formed. The solid was filtered and dried to afford 5-{1-[(2-fluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (73 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.26 (t, J=8.72 Hz, 2H), 3.73 (s, 3H), 3.93 (s, 2H), 4.28 (t, J=8.46 Hz, 2H), 7.19 (d, J=7.58 Hz, 3H), 7.26 (s, 1H), 7.30-7.38 (m, 3H), 8.09 (d, J=8.34 Hz, 1H), 8.14 (s, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08598156B2
Source datasetuspto-grants-2013_12
ORD IDord-9f1841a3fb7e40ca8544147796754a58
Source noteuspto-grants-2013_12