Dimethylacetamide → HCID 117987747, compound

HRID 2206203Notes

Reaction equation

Br[C:2]1[C:3]2[N:12]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])[N:11]=[C:10]([C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[CH:23][CH:22]=3)[C:4]=2[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C[C:34]([N:36](C)C)=O>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.[Zn+2].[C-]#N>[F:19][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([F:20])[C:13]=1[N:12]1[C:3]2[C:2]([C:34]#[N:36])=[CH:7][N:6]=[C:5]([O:8][CH3:9])[C:4]=2[C:10]([C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)=[CH:23][CH:22]=2)=[N:11]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-(4-(7-bromo-1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)phenyl)morpholine (93 mg) obtained in Step B of Example 218 in DMA (3 mL) were added tetrakis(triphenylphosphine)palladium(0) (43 mg) and zinc cyanide (33 mg) at room temperature, and the mixture was stirred under microwave irradiation at 120° C. for 30 min. The reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (77 mg).

Workup

customThe reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-b49eb652e87f4d2cbeca9de2e10d7347
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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