Sodium Carbonate → HCID 58759725, compound

HRID 859059Notes

Reaction equation

I[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[C:14]3[N:15]=[C:16]([NH2:18])[S:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH:32]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:36]([O:35][C:33]([N:30]1[CH2:29][CH:28]=[C:27]([C:2]2[CH:3]=[C:4]([O:8][C:9]3[C:14]4[N:15]=[C:16]([NH2:18])[S:17][C:13]=4[CH:12]=[CH:11][CH:10]=3)[N:5]=[CH:6][N:7]=2)[CH2:32][CH2:31]1)=[O:34])([CH3:39])([CH3:37])[CH3:38]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-(6-iodo-pyrimidin-4-yloxy)-benzothiazol-2-ylamine, (Example 129(b)), (200 mg, 0.54 mmol), 1,1-dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate (200 mg, 0.65 mmol, prepared according Eastwood, P. R. Tetrahedron Lett. 2000, 41, 3705–3708), PdCl2(PPh3)2 (38 mg, 0.050 mmol, Aldrich), and Na2CO3 (86 mg, 0.81 mmol) in DME/EtOH/H2O (2:1:2, 2.0 mL) was stirred and heated by microwave synthesizer at 120° C. for 15 min. The reaction mixture was concentrated in vacuum to dryness. Purification by silica gel chromatography (gradient: 0% to 5.0% MeOH/CH2Cl2) provided the title compound as a light-yellow solid. Mp: 188° C. (decomp.). MS (ESI, pos. ion) m/z: 426 (M+1).

Workup

concentrationThe reaction mixture was concentrated in vacuum to dryness
customPurification by silica gel chromatography (gradient: 0% to 5.0% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-5c59d5b3b00a482895c066831bfa291b
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148221B2

Reaction notes

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