Tert-butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamate → 2-(2-aminopyridin-3-yl)-4H-thieno[2,3-c]pyrrol-6(5H)-one

HRID 2091565Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[C:10]([NH:15]C(=O)OC(C)(C)C)=[N:11][CH:12]=[CH:13][CH:14]=2)O1.Br[C:25]1[S:33][C:28]2[C:29](=[O:32])[NH:30][CH2:31][C:27]=2[CH:26]=1>CCCCO.C([O-])([O-])=O.[Na+].[Na+].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>[NH2:15][C:10]1[C:9]([C:25]2[S:33][C:28]3[C:29](=[O:32])[NH:30][CH2:31][C:27]=3[CH:26]=2)=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of tert-butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carba mate (736 mg, 2.3 mmol), 2-bromo-4H-thieno[2,3-c]pyrrol-6(5H)-one (500 mg, 2.3 mmol) and Pd(PPh3)4 (40 mg, 0.035 mmol) in n-BuOH (5 mL) and 2.0 M Na2CO3 (4.6 mL) was degassed and the resulting reaction mixture was refluxed at 110° C. for 2 h. Upon completion, the reaction was cooled to room temperature, filtered, and washed with MeOH (10 mL) and water (2×10 mL). The solid was dried under high vacuum yielding 2-(2-aminopyridin-3-yl)-4H-thieno[2,3-c]pyrrol-6(5H)-one (383 mg, 72% yield) as a light brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.40 (br. s., 1H), 8.00 (dd, J=5.0, 1.8 Hz, 1H), 7.52 (dd, J=7.3, 1.8 Hz, 1H), 7.36 (s, 1H), 6.66 (dd, J=7.4, 4.9 Hz, 1H), 5.99 (s, 2H), 4.32 (s, 2H); MS (EI) m/z=232.3 [M+1]+.

Workup

customthe resulting reaction mixture
temperatureUpon completion, the reaction was cooled to room temperature
filtrationfiltered
washwashed with MeOH (10 mL) and water (2×10 mL)
customThe solid was dried under high vacuum

Sources & evidence

ORD record: ord-19e8b5c1411346f78f2f725983ee8e51
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440652B2

Reaction notes

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