Pyrrolidine → HCID 24856995, compound

HRID 1929947Notes

Reaction equation

HRID 1929947 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.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1B(O)O.[NH2:28][C@@H:29]([CH2:34][OH:35])[CH2:30][CH:31]([CH3:33])[CH3:32]>>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:8]1[C:7]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:6][CH:5]=[C:4]([CH:9]=1)[C:3]([NH:28][C@@H:29]([CH2:34][OH:35])[CH2:30][CH:31]([CH3:33])[CH3:32])=[O:12]

Participants

5

Reactant 4

HCID 31268PyrrolidineHCID 2724002D(-)-LeucinolHCID 27343542-Fluorophenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinate

Product 1

HCID 24856995HCID 24856995, 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), 2-fluorophenyl-boronic acid (commercially available) and (R)-(−)-leucinol (commercially available) as starting materials. MS (ISP): 386.4 (M+H+).

Workup

  1. customdescribed for the preparation of Example 43

Sources & evidence

ORD record
ord-6456ce02785f489286701fef8bfa78a3
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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