2-Fluorophenylboronic acid → 5-(2-fluorophenyl)-1H-pyrrolo[3,2-b]pyridine

HRID 1529342Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O>[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-chloro-1H-pyrrolo[3,2-b]pyridine (150 mg, 0.983 mmol, Matrix Scientific), 2-fluorophenylboronic acid (275 mg, 1.966 mmol, Aldrich) and dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium (II) (80 mg, 0.098 mmol, Strem) was capped, degassed and backfilled with argon (3×). Toluene (2 mL), EtOH (2 mL) and Na2CO3, 2.0 M (0.983 mL, 1.966 mmol) were added, and the reaction was heated to 120° C. in a microwave for 45 min. The solution was diluted with EtOAc (50 mL) and washed with brine (50 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluent: 1-4% MeOH/DCM), affording 5-(2-fluorophenyl)-1H-pyrrolo[3,2-b]pyridine (200 mg, 96%). MS (ESI, pos. ion) m/z: 213.1 (M+1).

Workup

customwas capped
customdegassed
additionToluene (2 mL), EtOH (2 mL) and Na2CO3, 2.0 M (0.983 mL, 1.966 mmol) were added
additionThe solution was diluted with EtOAc (50 mL)
washwashed with brine (50 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
custompurified by silica gel chromatography (eluent: 1-4% MeOH/DCM)

Sources & evidence

ORD record: ord-b366e8fc1c1945ba93327ddc84ee759b
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090593B2

Reaction notes

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