4-Bromobenzaldehyde → HCID 86660612, compound

HRID 717660Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1.OCC1SC(B(O)O)=CC=1>>[CH:26]([C:25]1[CH:28]=[CH:29][C:22]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:23][CH:24]=1)=[O:27]

Participants

Reactant 3

HCID 707414-Bromobenzaldehyde

HCID 43742655-Hydroxymethylthiophene-2-boronic acid

HCID 620032844-bromo-N-(3-methoxyphenyl)-N-methylbenzenesulfonamide

Product 1

HCID 86660612HCID 86660612, compoundYield 73%

Procedure

When the product of Step B and 4-carbaldehyde-boronic acid were substituted for 4-bromobenzaldehyde and 5-(hydroxymethyl)thiophen-2-ylboronic acid, respectively, in Example 22, Step A, the similar process afforded the title compound in 73% yield, as pale solid. 1H-NMR (CDCl3) 10.07 (s, 1H); 7.98 (d, 2H, J=6.56 Hz); 7.75 (d, 2H, J=8.24 Hz); 7.7 (d, 2H, J=8.82 Hz); 7.66 (d, 2H, J=8.75 Hz); 7.19 (t, 1H, J=8.13 Hz); 6.81 (dd, 1H, J=8.30, 2.45 Hz); 6.74 (t, 1H, J=2.17 Hz); 6.65 (dd, 1H, J=7.96, 1.24 Hz); 3.76 (s, 3H); 3.20 (s, 3H).

Sources & evidence

ORD record: ord-8d3517c857a94af8b73313a7af7fc389
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193716B2

Reaction notes

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