Cesium carbonate → HCID 67385834, compound

HRID 1408802Notes

Reaction equation

OC(C(F)(F)F)=O.[NH2:8][C:9]1[N:10]([CH3:31])[C:11](=[O:30])[C:12]2([N:29]=1)[C:21]1[C:16](=[CH:17][CH:18]=[C:19](Br)[CH:20]=1)[S:15][CH:14]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:13]2.[C:32]([C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1)#[N:33].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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>[NH2:8][C:9]1[N:10]([CH3:31])[C:11](=[O:30])[C:12]2([N:29]=1)[C:21]1[C:16](=[CH:17][CH:18]=[C:19]([C:38]3[CH:39]=[C:34]([CH:35]=[CH:36][CH:37]=3)[C:32]#[N:33])[CH:20]=1)[S:15][CH:14]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:13]2

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 2-amino-6′-bromo-1-methyl-2′-phenylspiro[imidazole-4,4′-thiochroman]-5(1H)-one TFA salt (70 mg, 0.14 mmol), 3-cyanophenylboronic acid (51 mg, 0.34 mmol), and Cs2CO3 (250 mg) in 1,4-dioxane (4 mL) and H2O (0.5 mL) charged in a 10 mL CEM microwave test tube is added PdCl2(PPh3)2 (20 mg). Then the system is degassed by sweeping with N2. The tube is capped and heated to 110° C. for 30 min in a CEM microwave reactor. Solvent is removed in vacuo and the residue is purified by preparative HPLC to give 3-(2-amino-1-methyl-5-oxo-2′-phenyl-1,5-dihydrospiro-[imidazole-4,4′-thiochroman]-6′-yl)benzonitrile (30 mg) as a TFA salt. MS ESI+ve m/z 425 (M+H)+.

Workup

customThen the system is degassed
customThe tube is capped
customSolvent is removed in vacuo
customthe residue is purified by preparative HPLC

Sources & evidence

ORD record: ord-f321c554285245e8bc6e60f41561e179
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921359B2

Reaction notes

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