Cesium carbonate → HCID 46833796, compound

HRID 1037001Notes

Reaction equation

HRID 1037001 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:14]([N:16]2[CH2:20][C:19](=[O:21])[NH:18][CH2:17]2)=[O:15])[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1.[C:22]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:29]=1[F:30])#[N:23].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:13][C:9]1[CH:8]=[C:7]([C:6]2[S:5][C:4]([C:14]([N:16]3[CH2:20][C:19](=[O:21])[NH:18][CH2:17]3)=[O:15])=[CH:3][C:2]=2[C:26]2[CH:27]=[CH:28][C:29]([F:30])=[C:24]([C:22]#[N:23])[CH:25]=2)[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 27579643-Cyano-4-fluorophenylboronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 580667401-{[4-Bromo-5-(3-chlorophenyl)thiophen-2-yl]carbonyl}imidazolidin-4-one

Product 1

HCID 46833796HCID 46833796, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

Under argon, 61.0 mg (0.16 mmol) of the compound from Example 24A are provided in 3 ml of 1,2-dimethoxyethane, and 26.1 mg (0.16 mmol) of 3-cyano-4-fluorophenylboronic acid, 155 mg (0.47 mmol) of cesium carbonate, 5.3 mg (0.01 mmol) of dicyclohexyl[2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosphane and 1.1 mg (0.005 mmol) of palladium(II) acetate are added. The mixture is heated in a closed glass vessel at 100° C. under microwave irradiation for 30 minutes. The reaction mixture is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 23.0 mg (34% of theory) of the title compound are obtained.

Workup

  1. customThe reaction mixture is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-80d990ba71a64f73bb1bd84f1f8c4f67
Source dataset
uspto-grants-2013_10
Patent number
US08546438B2

Reaction notes

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