3-Cyanophenylboronic acid → HCID 66607612, compound

HRID 1625761Notes

Reaction equation

C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([F:34])=[C:26]([CH2:35][C:36]2[S:37][C:38](Br)=[CH:39][CH:40]=2)[CH:25]=1)(=O)C.[C:42]([C:44]1[CH:45]=[C:46](B(O)O)[CH:47]=[CH:48][CH:49]=1)#[N:43]>>[C@@H:6]1([C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([F:34])=[C:26]([CH2:35][C:36]3[S:37][C:38]([C:48]4[CH:47]=[CH:46][CH:45]=[C:44]([C:42]#[N:43])[CH:49]=4)=[CH:39][CH:40]=3)[CH:25]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

Reactant 2

HCID 27343253-Cyanophenylboronic acid

HCID 66608049HCID 66608049, compound

Product 1

HCID 66607612HCID 66607612, compound

Procedure

The above 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-(5-bromo-2-thienylmethyl)-4-fluoronaphthalene and 3-cyanophenylboronic acid were treated in a manner similar to Example 168 to give 1-(β-D-glucopyranosyl)-3-(5-(3-cyanophenyl)-2-thienylmethyl)-4-fluoronaphthalene. APCI-Mass m/Z 523 (M+NH4).

Sources & evidence

ORD record: ord-4d3633ff20ba4ca9b7a0e66e4d2efc6a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785403B2

Reaction notes

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