Dimethylformamide → HCID 68295389, compound

HRID 1525841Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([O:8][C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[CH:10]=2)[CH:5]=[N:6][CH:7]=1.[CH3:20][N:21](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.[C-]#N.[C-]#N.[Zn+2]>[C:20]([C:2]1[CH:3]=[C:4]([O:8][C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[CH:10]=2)[CH:5]=[N:6][CH:7]=1)#[N:21]

Participants

Conditions

Temperature: 140 °C

Procedure

Methyl 4-(5-bromopyridin-3-yloxy)-6-methylpicolinate (313 mg, 0.969 mmol, 1.00 eq), Tetrakis(triphenylphosphine)palladium(0) (112 mg, 0.0969 mmol, 0.1 eq), Zn(CN)2 (125 mg, 1.06 mmol, 1.1 eq), and DMF (5 mL) were added to a microwave vial and heated at 140° C. for 10 minutes. The reaction was filtered and concentrated on silica gel (2 g). The silica gel was loaded on top a fresh bed of silica gel and washed with 50% ethyl acetate/hexane. The solvents were removed in vacuo and the crude solid was purified by flash chromatography on silica gel to afford 210 mg (81%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.97 (d, J=1.5 Hz, 1H), 8.84 (d, J=2.7 Hz, 1H), 8.35-8.34 (m, 1H), 7.45 (d, J=2.2 Hz, 1H), 7.21 (d, J=2.2 Hz, 1H), 3.85 (s, 3H), 2.49 (s, 3H); [M+1]+: 270.1.

Workup

filtrationThe reaction was filtered
concentrationconcentrated on silica gel (2 g)
washwashed with 50% ethyl acetate/hexane
customThe solvents were removed in vacuo
customthe crude solid was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-2b1667390576410797f221a099f7a10b
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085562B2

Reaction notes

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