Cesium carbonate → Trifluoroacetic acid

HRID 1408836Notes

Reaction equation

[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[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[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:44].[Cs+].[Cs+].O1CCO[CH2:51][CH2:50]1>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([C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:38]4[CH:39]=[C:34]([CH:35]=[CH:36][CH:37]=4)[C:32]#[N:33])[CH:20]=3)[O:44][CH:14]([CH:23]3[C:28]4[C:27](=[CH:50][CH:51]=[CH:2][CH:4]=4)[CH2:26][CH2:25][CH2:24]3)[CH2:13]2)[N:29]=1.[C:2]([OH:3])([C:4]([F:7])([F:6])[F:5])=[O:1]

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 (20 mg, 0.036 mmol), 3-cyanophenylboronic acid (7 mg, 0.047 mmol) and Cs2CO3 (30 mg, 0.092 mmol) in 1,4-dioxane (4 mL) and H2O (0.5 mL) charged in a 10 mL CEM microwave test tube was added PdCl2(PPh3)2 (3 mg, 0.004 mmol), then the system was degassed by sweeping N2. The tube was capped and heated to 110° C. for 10 min in a CEM microwave reactor. Solvent was removed in vacuum and the residue was purified by preparative HPLC to yield 4 isomers of the desired product as a TFA salt.

Workup

customthe system was degassed
customThe tube was capped
customSolvent was removed in vacuum
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-9a9873ebf1c14954ad201165ae4cdf26
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921359B2

Reaction notes

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