4-Bromobenzaldehyde → 4-(12-Oxo-12H-chromeno[2,3-b]quinolin-2-yl)benzaldehyde

HRID 717683Notes

Reaction equation

HRID 717683 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[O:16][C:7]1=[N:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=[C:6]1[C:5]2=[O:20].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>>[O:20]=[C:5]1[C:6]2[C:7](=[N:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=2)[O:16][C:17]2[C:4]1=[CH:3][C:2]([C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1)=[CH:19][CH:18]=2

Participants

4

Reactant 3

HCID 707414-BromobenzaldehydeHCID 43742655-Hydroxymethylthiophene-2-boronic acidHCID 666150262-Bromo-12H-chromeno[2,3-b]quinolin-12-one

Product 1

HCID 866606214-(12-Oxo-12H-chromeno[2,3-b]quinolin-2-yl)benzaldehydeYield 52%

Procedure

When the product of Step B and 4-carbaldehyde-boronic were substituted for 4-bromobenzaldehyde and 5-(hydroxymethyl)thiophen-2-ylboronic acid, respectively, in Example 22, Step A, the similar procedure afforded the title compound in 52% yield, as off white solid. 1H-NMR (CDCl3) 10.08 (s, 1H); 9.33 (s, 1H); 8.6 (d, 1H, J=2.34 Hz); 8.14-8.05 (m, 3H); 8.00 (d, 2H, J=8.25 Hz); 7.96-7.89 (m, 1H); 7.85 (d, 2H, J=8.22 Hz); 7.74 (d, 1H, J=8.7 Hz); 7.64 (t, 1H, J=7.8 Hz).

Sources & evidence

ORD record
ord-f2edb6f20ae9477d827bdd58f8a4b61b
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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