Potassium Carbonate → 1-((2'-(t-butylaminosulfonyl)-3-fluoro-(1,1'-biphenyl)-4-yl)methyl)-2-(n-propyl)-4-ethyl-5-(2-(phenoxy)phenoxy)acetyl-1H-imidazole

HRID 1078051Notes

Reaction equation

HRID 1078051 reaction equation
Br[C:2]1[CH:35]=[CH:34][C:5]([CH2:6][N:7]2[C:11]([C:12](=[O:28])[CH2:13][O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:10]([CH2:29][CH3:30])[N:9]=[C:8]2[CH2:31][CH2:32][CH3:33])=[C:4]([F:36])[CH:3]=1.[C:37]([NH:41][S:42]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1B(O)O)(=[O:44])=[O:43])([CH3:40])([CH3:39])[CH3:38].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:37]([NH:41][S:42]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[C:2]1[CH:35]=[CH:34][C:5]([CH2:6][N:7]2[C:11]([C:12](=[O:28])[CH2:13][O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[C:10]([CH2:29][CH3:30])[N:9]=[C:8]2[CH2:31][CH2:32][CH3:33])=[C:4]([F:36])[CH:3]=1)(=[O:44])=[O:43])([CH3:40])([CH3:39])[CH3:38]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-HCID 194304711-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-(2-(phenoxy)phenoxy)acetyl-1H-imidazole

Product 1

HCID 194304481-((2'-(t-butylaminosulfonyl)-3-fluoro-(1,1'-biphenyl)-4-yl)methyl)-2-(n-propyl)-4-ethyl-5-(2-(phenoxy)phenoxy)acetyl-1H-imidazoleYield 40.3%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

From 0.16 g (0.29 mmol) of 1-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-(2-(phenoxy)phenoxy)acetyl-1H-imidazole, using 0.12 g (0.47 mmol) of 2-(t-butylamino)sulfonylphenyl boronic acid, 0.12 g (0.86 mmol)potassium carbonate, 0.016 g (0.05 mmol) tetrabutylammonium bromide, 0.02 g (0.02 mmol) tetrakis(triphenylphosphine)palladium(0), with 1 mL of water and 2 mL of toluene as solvent, 0.08 g (40%) of the title compound was obtained following the procedure of Example 3, Part F, after purification by preparative TLC (silica gel; 20% acetone, 30% ethyl acetate, 50% hexane). 1H NMR (300 MHz, CDCl3): δ 0.97 (m, 12H, overlapping t-butyl singlet and methyl triplet); 1.32 (t, 3H, J=7.3 Hz); 1.72 (m, 2H); 2.63 (t, 2H, J=7.3 Hz); 2.83 (q, 2H, J=7.3 Hz); 3.57 (s, 1H); 5.06 (s, 2H); 5.58 (s,2H); 6.61 (t, 1H, J=8.1 Hz); 6.87-7.09 (m, 7H); 7.12 (d, 1H, J=8.1 Hz); 7.23-7.29 (m,5H); 7.51 (m, 2H); 8.15 (d, 1H, J=7.7 Hz). ##STR107##

Sources & evidence

ORD record
ord-f9b7e94387234e0481ecacf5270fc192
Source dataset
uspto-grants-1996_08
Patent number
US05545651

Reaction notes

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