Sodium Carbonate → HCID 72549195, compound

HRID 1022440Notes

Reaction equation

Cl[C:2]1[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][N:11]([CH2:12]C)[C:4]=2[CH:3]=1.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.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>[CH3:12][N:11]1[C:4]2[CH:3]=[C:2]([C:19]3[CH:20]=[CH:21][C:16]([C:15]([F:26])([F:25])[F:14])=[CH:17][CH:18]=3)[NH:7][C:6](=[O:8])[C:5]=2[CH:9]=[CH:10]1

Participants

Conditions

Temperature: 140 °C

Procedure

A microwave reaction vial was charged with 6-chloro-1-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridine-4-one (Intermediate G) (16 mg, 0.08 mmol), 4-(trifluoromethyl)phenylboronic acid (20 mg, 0.10 mmol), tetrakis(triphenylphosphine)palladium(0) (5.06 mg, 0.004 mmol), and 2M aqueous sodium carbonate solution (0.13 mL) in ethanol (2 mL). The vial was sealed and then heated in a microwave at 140° C. for 10 min. At this time, the resulting mixture was filtered through a pad of Celite® and concentrated in vacuo. Flash chromatography (20/1 methylene chloride/methanol) afforded 1-methyl-6-(4-trifluoromethyl-phenyl)-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one (25.6 mg, 39.1%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.8 (s, 3H) 6.5 (d, J=3.01 Hz, 1H) 7.0 (s, 1H) 7.1 (d, J=3.01 Hz, 1H) 7.8 (d, J=8.28 Hz, 2H) 8.0 (d, J=8.28 Hz, 2H) 11.1 (br. s., 1H). LC-MS calcd. for C15H12F3N2O [(M+H)+] 293, obsd. 293.0.

Workup

customA microwave reaction
customThe vial was sealed
filtrationAt this time, the resulting mixture was filtered through a pad of Celite®
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6b6846b2c7fa4361b35a72a4634471a3
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722661B2

Reaction notes

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