Sodium Carbonate → HCID 178452596, compound

HRID 872320Notes

Reaction equation

[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[C:24](Br)[CH:23]=[CH:22][N:21]4[C:27]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(OC([N:42]1[C:46](B(O)O)=[CH:45][CH:44]=[N:43]1)=O)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+].[NH4+].[Cl-]>O1CCOCC1.C(Cl)Cl.O>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[C:24]([C:46]5[CH:45]=[CH:44][NH:43][N:42]=5)[CH:23]=[CH:22][N:21]4[C:27]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 105 °C

Procedure

To a solution of {1-[4-(7-bromo-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (200 mg, 0.38 mmol), and 1-(tert-butoxycarbonyl)pyrazole-5-boronic acid (164 mg, 0.77 mmol, 2 equiv) in dioxane (4 mL) under argon was added [1,1-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) CH2Cl2 complex (63 mg, 0.77 mmol, 20 mol %), Na2CO3 (123 mg, 1.16 mmol, 3 equiv) and water (0.5 mL). The resulting mixture was heated at 105° C. for 8 h in a microwave apparatus. The reaction mixture was mixed with water (10 mL), a saturated aqueous NH4Cl solution (10 mL) and CH2Cl2 (25 mL) with vigorous stirring at room temperature for 30 min. The organic phase was washed with a saturated aqueous NaCl solution (25 mL), dried (Na2SO4 anh), and concentrated under reduced pressure.

Workup

washThe organic phase was washed with a saturated aqueous NaCl solution (25 mL)
dry with materialdried (Na2SO4 anh)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9333544ff08c4662b0e2f8f035742928
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975265B2

Reaction notes

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