Dimethylformamide → HCID 58746070, compound

HRID 723726Notes

Reaction equation

[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:9]2[N:10]([N:15]=[CH:16][CH:17]=2)[C:11](I)=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:19][N:20](C=O)C>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:9]2[N:10]([N:15]=[CH:16][CH:17]=2)[C:11]([C:19]#[N:20])=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (7-iodo-pyrazolo[1,5-a]pyridin-4-yl)-carbamic acid tert-butyl ester (36 mg, 0.1 mmol), zinc cyanide (24 mg, 0.2 mmol), tetrakis(triphenylphosphine) palladium (0) (23 mg, 0.02 mmol), and anhydrous DMF (1 mL) was degassed with argon. Then, the mixture was stirred at 80° C. for 4.5 h, cooled to rt, mixed with EtOAc (6 mL), and filtered. The filtrate was concentrated under reduced pressure. Purification by silica gel flash chomatography eluting with EtOAc/heptane (gradient from 1:4 to 1:2 ratio) gave compound 777E (24 mg, 93%) as a white solid. HPLC: 93% at 3.64 min (retention time) (YMC S5 ODS-A column 4.6×50 mm eluting with 10–90% aqueous methanol over 4 mincontaining 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 259 [M+H]+.

Workup

customwas degassed with argon
temperaturecooled to rt
additionmixed with EtOAc (6 mL)
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
customPurification by silica gel flash chomatography
washeluting with EtOAc/heptane (gradient from 1:4 to 1:2 ratio)

Sources & evidence

ORD record: ord-e5b12fb7d30045ae88285106a3554e38
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141578B2

Reaction notes

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