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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2410895Generated: November 2, 2026

Toluene → HCID 66604909, compound

https://huagongshe.com/reaction/2410895

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantSodium CarbonateHCID 10340—
ReactantPhenylboronic AcidHCID 66827—
ReactantHCID 66604304HCID 66604304—
CatalystHCID 178418397HCID 178418397—
SolventMethanolHCID 887—
ProductHCID 66604909HCID 6660490939.4%

Reaction Conditions

Temperature105 °C

Reaction Steps

3-Bromo-4-fluoro-6-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide (25 mg, 0.059 mmol), phenylboronic acid (10.88 mg, 0.089 mmol), Pd(Ph3P)4 (6.87 mg, 5.95 μmol) and Na2CO3(2M) (0.074 mL, 0.149 mmol) were mixed with toluene (2 mL) and MeOH (1 mL) in a sealed microwave tube. The mixture was stirred at 105° C. for 3 hrs. The mixture was filtered through a ACRODISC® PTFE membrane (0.45 um) and purified using preparative HPLC to give 9.7 mg of 4-fluoro-6-(morpholine-4-carbonyl)-3-phenyl-9H-carbazole-1-carboxamide. MS (ESI) m/z 418.06 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.9 (bs, 1H), 8.32 (bs, 1H), 8.19 (d, 1H, J=7.1), 8.15 (s, 1H), 7.84 (d, 1H, J=8.6), 7.72 (d, 2H, J=7.3), 7.62-7.53(m, 4H), 7.43 (t, 1H, J=7.3), 3.7-3.5 (bm, 8H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08815840B2
Source datasetuspto-grants-2014_08
ORD IDord-757ab63009254bf98145a520b6abfcd1
Source noteuspto-grants-2014_08