Cesium carbonate → HCID 67451804, compound

HRID 869202Notes

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.[S:28]1[C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][N:30]=[CH:29]1.CC(P(C(C)(C)C)C1C(C2C=CC=CC=2)=CC=CC=1)(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:11]([O:10][C:9]([N:8]([CH2:16][C:17]1([C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:20][CH2:19][CH2:18]1)[C:5]1[N:6]=[N:7][C:2]([C:29]2[S:28][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][N:30]=2)=[CH:3][CH:4]=1)=[O:15])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 145 °C

Procedure

tert-butyl 6-chloropyridazin-3-yl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)carbamate (500 mg, 1.27 mmol), ethyl thiazole-5-carboxylate (300 mg, 1.91 mmol), Pd(OAc)2 (86 mg, 0.13 mmol), JohnPhos (92 mg, 0.26 mmol) and Cs2CO3 (827 mg, 2.54 mmol) in toluene (10 mL) were combined and heated in a microwave reactor for 30 min at 145° 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 yellow oil (162 mg, 82% pure, 21%), LRMS (M+H+) m/z 514.3.

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-a520da7a6a2a47a38ca51688c8405fea
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969346B2

Reaction notes

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