4-Chlorophenylboronic acid → HCID 24856673, compound

HRID 1929846Notes

Reaction equation

HRID 1929846 reaction equation
CO[C:3]([C:5]1[CH:6]=[N:7][C:8](Cl)=[C:9](Br)[CH:10]=1)=[O:4].[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.[CH3:23][C@@H:24]([OH:27])[CH2:25][CH3:26].[NH2:28][C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]1[OH:35]>>[C@H:24]([O:27][C:8]1[C:9]([C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=2)=[CH:10][C:5]([C:3]([NH:28][C@@H:29]2[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]2[OH:35])=[O:4])=[CH:6][N:7]=1)([CH2:25][CH3:26])[CH3:23]

Participants

5

Reactant 4

HCID 742994-Chlorophenylboronic acidHCID 84682(-)-2-ButanolHCID 735777(1R,2R)-2-AminocyclohexanolHCID 2764313Methyl 5-bromo-6-chloronicotinate

Product 1

HCID 24856673HCID 24856673, compound

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 5, using 5-bromo-6-chloro-3-pyridinecarboxylic acid methyl ester, 4-chlorophenyl-boronic acid (commercially available), (R)-(−)-2-butanol (commercially available), and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials. MS (ISP): 403.5 (M+H+).

Workup

  1. customdescribed for the preparation of Example 5

Sources & evidence

ORD record
ord-78135e026f2c4dadb16846a5ac98b361
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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