Potassium Carbonate → HCID 68231539, compound

HRID 869207Notes

Reaction equation

Cl[C:2]1[N:7]=[N:6][C:5]([N:8]([CH2:16][C:17]2([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][N:22]=3)[CH2:20][CH2:19][CH2:18]2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[C:28]([C:30]1[S:34][C:33](B(O)O)=[CH:32][CH:31]=1)#[N:29].C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[C:28]([C:30]1[S:34][C:33]([C:2]2[N:7]=[N:6][C:5]([N:8]([CH2:16][C:17]3([C:21]4[C:26]([F:27])=[CH:25][CH:24]=[CH:23][N:22]=4)[CH2:18][CH2:19][CH2:20]3)[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[CH:4][CH:3]=2)=[CH:32][CH:31]=1)#[N:29]

Participants

Conditions

Temperature: 140 °C

Procedure

t-Butyl 6-chloropyridazin-3-yl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)carbamate (900 mg, 2.29 mmol, 1 equiv), 5-cyanothiophen-2-ylboronic acid (390 mg, 2.52 mmol, 1.1 equiv), (dppf)PdCl2 (164 mg, 0.23 mmol, 0.1 equiv), nitrogen-sparged dioxane (6.0 mL) and aq. 2 N K2CO3 (2.3 mL) were combined and heated in a microwave reactor for 30 min at 140° C. The reaction mixture was filtered through a Celite plug and the filtrate was concentrated. The resulting residue was purified on silica gel using a mixture of ethyl acetate and hexanes to provide the title compound as a yellow oil (340 mg, 32%), LRMS (M+H+) m/z 466.3.

Workup

filtrationThe reaction mixture was filtered through a Celite plug
concentrationthe filtrate was concentrated
customThe resulting residue was purified on silica gel using
additiona mixture of ethyl acetate and hexanes

Sources & evidence

ORD record: ord-e5ffe06bd8ab4359aa40bdc2a1b07d9a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969346B2

Reaction notes

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