4-Bromobenzaldehyde → HCID 86660613, compound

HRID 717665Notes

Reaction equation

HRID 717665 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]([CH:15]([CH3:17])[CH3:16])[C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1.OCC1SC(B(O)O)=CC=1>>[F:14][C:11]1[CH:12]=[CH:13][C:8]([N:7]([CH2:6][C:5]2[CH:18]=[CH:19][C:2]([C:21]3[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=3)=[CH:3][CH:4]=2)[CH:15]([CH3:17])[CH3:16])=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 707414-BromobenzaldehydeHCID 43742655-Hydroxymethylthiophene-2-boronic acidHCID 66614972N-(4-Bromobenzyl)-4-fluoro-N-isopropylbenzenamine

Product 1

HCID 86660613HCID 86660613, compoundYield 65%

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 65% yield, as creamy gum. 1H-NMR (CDCl3) 10.03 (s, 1H); 7.92 (d, 2H, J=7.97 Hz); 7.56 (d, 2H, J=7.95 Hz); 7.38 (d, 2H, J=8.29 Hz); 6.86 (t, 2H, J=8.46 Hz); 6.67-6.62 (m, 2H); 4.38 (s, 2H); 4.17-4.12 (m, 1H); 1.2 (d, 6H, J=6.96 Hz).

Sources & evidence

ORD record
ord-451edd8969e24be5b06a1e84a176b92e
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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