Pyrrolidine → HCID 24857435, compound

HRID 1929946Notes

Reaction equation

HRID 1929946 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7](Cl)=[N:6][CH:5]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][C:20]=1[CH3:28].[NH2:29][C@H:30]([CH2:35][OH:36])[CH2:31][CH:32]([CH3:34])[CH3:33]>>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:8]2[C:7]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[N:6][CH:5]=[C:4]([CH:9]=2)[C:3]([NH:29][C@H:30]([CH2:35][OH:36])[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:12])=[CH:21][C:20]=1[CH3:28]

Participants

5

Reactant 4

HCID 31268PyrrolidineHCID 111307L-LeucinolHCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 3786632(4-Chloro-3-methylphenyl)boronic acid

Product 1

HCID 24857435HCID 24857435, compound

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 43, using 5-bromo-6-chloro-nicotinic acid methyl ester, pyrrolidine (commercially available), 4-chloro-3-methylphenyl-boronic acid (commercially available) and (S)-(+)-leucinol (commercially available) as starting materials. MS (ISP): 416.3 (M+H+).

Workup

  1. customdescribed for the preparation of Example 43

Sources & evidence

ORD record
ord-f7f5b368909149e49c5114f9810d450f
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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