N-(5-bromo-2-fluorophenyl)acetamide → N-{4-fluoro-4'-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl}acetamide

HRID 1059177Notes

Reaction equation

HRID 1059177 reaction equation
[OH:1][C:2]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)([C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1)[CH:3]([CH3:5])[CH3:4].Br[C:40]1[CH:41]=[CH:42][C:43]([F:50])=[C:44]([NH:46][C:47](=[O:49])[CH3:48])[CH:45]=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>[F:50][C:43]1[CH:42]=[CH:41][C:40]([C:33]2[CH:34]=[CH:35][C:30]([C:2]([OH:1])([C:6]3[N:7]=[CH:8][N:9]([C:11]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:10]=3)[CH:3]([CH3:5])[CH3:4])=[CH:31][CH:32]=2)=[CH:45][C:44]=1[NH:46][C:47](=[O:49])[CH3:48]

Participants

4

Reactant 2

HCID 242827N-(5-bromo-2-fluorophenyl)acetamideHCID 186685784-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]phenylboronic acid

Product 1

HCID 18668557N-{4-fluoro-4'-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl}acetamideYield 45.2%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

By the reaction in the same manner as in Example 4-(ii) using 4-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]phenylboronic acid (3.50 g), N-(5-bromo-2-fluorophenyl)acetamide (1.17 g) and tetrakis(triphenylphosphine)palladium(0) (0.17 g), the title compound (1.39 g); was obtained as a colorless amorphous powder.

Workup

  1. customBy the reaction in the same manner as in Example

Sources & evidence

ORD record
ord-a8b643a422024375bff9db7df1a49821
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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