3-bromo-N-cyclopropylbenzamide → N-cyclopropyl-4'-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-carboxamide

HRID 1059207Notes

Reaction equation

HRID 1059207 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]=[C:42]([CH:49]=[CH:50][CH:51]=1)[C:43]([NH:45][CH:46]1[CH2:48][CH2:47]1)=[O:44]>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>[CH:46]1([NH:45][C:43]([C:42]2[CH:41]=[C:40]([C:33]3[CH:32]=[CH:31][C:30]([C:2]([OH:1])([C:6]4[N:7]=[CH:8][N:9]([C:11]([C:12]5[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=5)([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=5)[CH:10]=4)[CH:3]([CH3:4])[CH3:5])=[CH:35][CH:34]=3)[CH:51]=[CH:50][CH:49]=2)=[O:44])[CH2:48][CH2:47]1

Participants

4

Reactant 2

HCID 8961523-bromo-N-cyclopropylbenzamideHCID 186685784-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]phenylboronic acid

Product 1

HCID 18668572N-cyclopropyl-4'-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-carboxamideYield 46.7%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

By the reaction in the same manner as in Example 33-(ii) using 4-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]phenylboronic acid (3.40 g), 3-bromo-N-cyclopropylbenzamide (1.53 g) and tetrakis(triphenylphosphine)palladium(0) (0.290 g), the title compound (1.84 g) was obtained as a pale-yellow amorphous powder.

Sources & evidence

ORD record
ord-a48a4bb5a62e46f6959e8bbf0beb5f9e
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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