Dimethylformamide → 3-[3-(1-Quinolin-6-ylcyclopropyl) [1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzonitrile

HRID 1099035Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([C:14]([C:17]4([C:20]5[CH:21]=[C:22]6[C:27](=[CH:28][CH:29]=5)[N:26]=[CH:25][CH:24]=[CH:23]6)[CH2:19][CH2:18]4)=[N:15][N:16]=3)[N:13]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:30][N:31](C=O)C>[C-]#N.[Zn+2].[C-]#N.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.[Zn]>[N:26]1[C:27]2[C:22](=[CH:21][C:20]([C:17]3([C:14]4[N:12]5[N:13]=[C:8]([C:4]6[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=6)[C:30]#[N:31])[CH:9]=[N:10][C:11]5=[N:16][N:15]=4)[CH2:19][CH2:18]3)=[CH:29][CH:28]=2)[CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 6-{1-[6-(3-bromophenyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-yl]cyclopropyl}quinoline (Example 40, 10 mg, 0.02 mmol), zinc cyanide (3.24 mg, 0.0271 mmol), bis(tri-t-butylphosphine)palladium (7 mg, 0.01 mmol), and zinc powder (1.77 mg, 0.0271 mmol) in DMF (0.6 mL) was heated at 170° C. for 20 min under microwave. After cooling to ambient temperature, the mixture was filtered. The filtrate was diluted with methanol and subject to preparative RP-HPLC (pH=10) to afford the desired product. Analytical LCMS: (M+H)+=390.2.

Workup

temperatureAfter cooling to ambient temperature
filtrationthe mixture was filtered
additionThe filtrate was diluted with methanol

Sources & evidence

ORD record: ord-821aef1176df4876bac1b70fc532c214
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143251B2

Reaction notes

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