3-Pyridinylboronic acid → HCID 68571254, compound

HRID 1435106Notes

Reaction equation

Br[C:2]1[CH:37]=[CH:36][C:5]2[N:6]([C:9]3[S:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[C:11]([O:18][C@@H:19]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][Si](C(C)(C)C)(C)C)[C:22]=4[Cl:35])[CH3:20])[CH:10]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1.[N:38]1[CH:43]=[CH:42][CH:41]=[C:40](B(O)O)[CH:39]=1>>[Cl:35][C:22]1[C:23]([OH:27])=[CH:24][CH:25]=[CH:26][C:21]=1[C@H:19]([O:18][C:11]1[CH:10]=[C:9]([N:6]2[C:5]3[CH:36]=[CH:37][C:2]([C:40]4[CH:39]=[N:38][CH:43]=[CH:42][CH:41]=4)=[CH:3][C:4]=3[N:8]=[CH:7]2)[S:13][C:12]=1[C:14]([O:16][CH3:17])=[O:15])[CH3:20]

Participants

Reactant 2

HCID 27343783-Pyridinylboronic acid

HCID 68567890HCID 68567890, compound2×

Product 1

HCID 68571254HCID 68571254, compoundYield 53%

Procedure

Methyl 5-(5-bromo-1H-benzimidazol-1-yl)-3-{[(1R)-1-(2-chloro-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}phenyl)ethyl]oxy}-2-thiophenecarboxylate (Intermediate 8, 500 mg, 0.80 mmol) and pyridine-3-boronic acid (120 mg, 0.96 mmol) were coupled using a procedure analogous to Intermediate 9 to give 213 mg of the title compound (53%). MS m/z=506 [M+H]+.

Sources & evidence

ORD record: ord-229cb13e1e554eebbcfc5ef490c439f0
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615643B2

Reaction notes

Loading…