Potassium Carbonate → HCID 16730183, compound

HRID 545590Notes

Reaction equation

HRID 545590 reaction equation
[CH3:1][O:2][C:3](=[O:40])[N:4]([CH2:25][C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=1)[CH2:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:7]=1B1OC(C)(C)C(C)(C)O1.[Cl:41][C:42]1[CH:47]=[C:46]([C:48]([O:50][CH3:51])=[O:49])[CH:45]=[CH:44][C:43]=1[C:52]1[CH:57]=[C:56](I)[C:55]([O:59][CH3:60])=[CH:54][C:53]=1[F:61].C(=O)([O-])[O-].[K+].[K+]>ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[F:39][C:36]([F:38])([F:37])[C:28]1[CH:27]=[C:26]([CH:31]=[C:30]([C:32]([F:34])([F:35])[F:33])[CH:29]=1)[CH2:25][N:4]([CH2:5][C:6]1[CH:11]=[C:10]([C:12]([F:14])([F:13])[F:15])[CH:9]=[CH:8][C:7]=1[C:56]1[CH:57]=[C:52]([C:43]2[CH:44]=[CH:45][C:46]([C:48]([O:50][CH3:51])=[O:49])=[CH:47][C:42]=2[Cl:41])[C:53]([F:61])=[CH:54][C:55]=1[O:59][CH3:60])[C:3]([O:2][CH3:1])=[O:40]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 57692977HCID 57692977, compoundHCID 57692979HCID 57692979, compound

Product 1

HCID 16730183HCID 16730183, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Methyl[3,5-bis(trifluoromethyl)benzyl][2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)benzyl]carbamate (100 mg, 0.171 mmol), methyl 2-chloro-2′-fluoro-5′-iodo-4′-methoxybiphenyl-4-carboxylate (71.9 mg, 0.171 mmol), 1,1′-bis(diphenylphosphino) ferrocene-palladium dichloride dichloromethane adduct (13.95 mg, 0.017 mmol), potassium carbonate (0.256 ml, 0.513 mmol) and 1,4-dioxane (1 ml) were sealed and subjected to microwave irradiation for 30 min at 140° C. An aliquot indicated formation of the desired product. The crude reaction mixture was dried over Na2SO4. The resulting dark mixture was purified by preparative TLC (silica gel) developed by EtOAc/hexanes (20%, v/v) mixture to give a green glass as the title compound. LCMS calc.=751.12; found=752.36 (M+1)+.

Workup

  1. customirradiation for 30 min at 140° C

Sources & evidence

ORD record
ord-20762cbcabda47afa19a6efc22553d34
Source dataset
uspto-grants-2011_05
Patent number
US07935727B2

Reaction notes

Loading…