Pyrrolidine → HCID 24857345, compound

HRID 1929922Notes

Reaction equation

HRID 1929922 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.[C:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)#[N:19].[NH2:29][C@@H:30]([CH2:35][OH:36])[CH2:31][CH:32]([CH3:34])[CH3:33]>>[C:18]([C:20]1[CH:25]=[CH:24][C:23]([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:22][CH:21]=1)#[N:19]

Participants

5

Reactant 4

HCID 31268PyrrolidineHCID 2724002D(-)-LeucinolHCID 27343264-Cyanophenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinate

Product 1

HCID 24857345HCID 24857345, 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-cyanophenyl-boronic acid (commercially available) and (R)-(−)-leucinol (commercially available) as starting materials. MS (ISP): 393.4 (M+H+).

Workup

  1. customdescribed for the preparation of Example 43

Sources & evidence

ORD record
ord-c9d26de00be541d0b4d4ffab231c7f47
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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