2-Chloropyridin-4-amine → 1-[4-(4-amino-2-pyridyl)phenyl]-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol

HRID 1059242Notes

Reaction equation

HRID 1059242 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].[NH2:39][C:40]1[CH:45]=[CH:44][N:43]=[C:42](Cl)[CH:41]=1.[Br-].[Na+]>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>[NH2:39][C:40]1[CH:45]=[CH:44][N:43]=[C:42]([C:33]2[CH:34]=[CH:35][C:30]([C:2]([C:6]3[N:7]=[CH:8][N:9]([C:11]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:10]=3)([OH:1])[CH:3]([CH3:5])[CH3:4])=[CH:31][CH:32]=2)[CH:41]=1

Participants

5

Reactant 3

HCID 844322-Chloropyridin-4-amineHCID 253881Sodium BromideHCID 186685784-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]phenylboronic acid

Product 1

HCID 186685231-[4-(4-amino-2-pyridyl)phenyl]-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanolYield 53.7%

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 (5.78 g), 4-amino-2-chloropyridine (1.00 g), sodium bromide (810 mg) and tetrakis(triphenylphosphine)palladium(0) (0.190 g), the title compound (2.30 g) was obtained as a yellow amorphous powder.

Sources & evidence

ORD record
ord-6828dc973dda4c758883092eb0a5ade3
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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