Water → HCID 71503403, compound

HRID 2274944Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-(5-Acetyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl)-benzonitrile (3a) (0.48 g, 1.8 mmol), 2,4-difluorobenzyl bromide (0.41 g, 1.99 mmol) and K2CO3 (498 mg, 3.6 mmol) in 14 ml CH3CN was stirred at 80° C. for 16 h. A second portion of 2,4-difluorobenzyl bromide (0.41 g, 1.99 mmol) was added and the mixture was stirred for additional 7 h. Water was added, the mixture was extracted 3 times with ethyl acetate, the combined organic layers were dried over MgSO4, filtrated and the solution was evaporated to dryness. The crude product was crystallized from 10 ml 2-propanol and dried in vacuo to give 0.364 g of 3-[5-Acetyl-1-(2,4-difluoro-benzyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (6a).

Workup

stirringthe mixture was stirred for additional 7 h
extractionthe mixture was extracted 3 times with ethyl acetate
dry with materialthe combined organic layers were dried over MgSO4
filtrationfiltrated
customthe solution was evaporated to dryness
customThe crude product was crystallized from 10 ml 2-propanol
customdried in vacuo

Sources & evidence

ORD record: ord-ef98fa85439a48ed96e3b459af40e276
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09127001B2

Reaction notes

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