2-Amino-4-bromobenzonitrile → tert-Butyl 4-(3-amino-4-cyanophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1406622Notes

Reaction equation

HRID 1406622 reaction equation
O=C1[NH:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([C:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:13]=3)=[CH:7][CH:8]=2)[NH:3]1.NC1C=C(Br)C=CC=1C#N.B([O-])[O-]>>[NH2:3][C:4]1[CH:5]=[C:6]([C:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:13]=2)[CH:7]=[CH:8][C:9]=1[C:10]#[N:11]

Participants

4

Reactant 3

HCID 99206362-Amino-4-bromobenzonitrileHCID 117796386tert-Butyl 4-(2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl)-5,6-dihydropyridine-1(2H)-carboxylateHCID 178514824HCID 178514824, compound

Product 1

HCID 117796387tert-Butyl 4-(3-amino-4-cyanophenyl)-5,6-dihydropyridine-1(2H)-carboxylateYield 62%

Procedure

Following the same procedure adopted for the synthesis of 22, the reaction of nitrile 11 with boronic ester 21 afforded the title compound 24 as an off-white solid (62%). IR (KBr) νmax. cm−1: 3421, 3318 (NH2), 3072 (Ar—H), 2247 (CN), 1691 (C═O), 1616, 1510, 1412 (C═C). 1H-NMR (500 MHz, CDCl3) δ=1.49 (s, 9H, (CH3)3C); 1.71 (br. s, 2H, CH2); 2.45 (br. s, 2H, CH2); 3.61 (m, 2H, CH2); 4.07 (s, 2H CH2); 4.43 (br. s, 2H, NH2); 6.10 (br. s, 1H, CH); 6.71 (d, J=2.2 Hz, 1H, H-2); 6.75 (dd, 1H, J=2.3, 8.6 Hz, H-6); 7.33 (d, J=8.5 Hz, 1H, H-5); 8.01 (br. s, 1H, NH); 13C NMR (125.7 MHz, CDCl3) δ=27.35 (CH2), 28.47 (CH3)3C), 29.73 (CH2), 41.96 (CH2), 79.91 (CH3)3C), 94.63 (aromatic-C), 115.12 (aromatic-C), 117.69 (CN), 133.67 (aromatic-C), 147.42 (aromatic-C), 150.47 (aromatic-C), 155.33 (C═O). Calculated (%) for C17H21N3O2 (299.16); C, 68.20; H, 7.07; N, 14.04. found (%; C, 68.16; H, 7.13; N, 13.97.

Sources & evidence

ORD record
ord-606576d48f75439c8c3e108c950cfe39
Source dataset
uspto-grants-2014_12
Patent number
US08916704B1

Reaction notes

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