4-(Tributylstannyl)pyridazine → HCID 67977266, compound

HRID 1184760Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20](Cl)[CH:21]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:29]1[CH:34]=[CH:33][N:32]=[N:31][CH:30]=1)CCC>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20]([C:29]4[CH:34]=[CH:33][N:32]=[N:31][CH:30]=4)[CH:21]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-(5-chloro-2,3-dihydro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (50 mg) and 4-(tributylstannyl)pyridazine (60 mg) in N,N-dimethylformamide (1 mL) is sparged with argon for 10 min and Pd(PPh3)3 (16 mg) is added. The resulting mixture is heated in an oil bath to 120° C. for 7 h. Ethyl acetate and water are added and the organic phase is separated, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (dichloromethane/methanol 95:5→90:10). The crude product is triturated with diethyl ether, filtered off, and dried to give the title compound. LC (method 7): tR=1.35 min; Mass spectrum (ESI+): m/z=383 [M+H]+.

Workup

customis sparged with argon for 10 min
additionPd(PPh3)3 (16 mg) is added
additionEthyl acetate and water are added
customthe organic phase is separated
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue is chromatographed on silica gel (dichloromethane/methanol 95:5→90:10)
customThe crude product is triturated with diethyl ether
filtrationfiltered off
customdried

Sources & evidence

ORD record: ord-27e599dd1c0b46c0b65e84ed95271598
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669271B2

Reaction notes

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