4'-Bromo-[1,1'-biphenyl]-4-carbaldehyde → Benzyl 2-(Benzyloxy)-4-(((4'-Bromo-[1,1'-Biphenyl]-4-Yl)Methyl)Amino)Benzoate

反応式

[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[C:4]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:3]=1.[Br:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([CH:39]=O)=[CH:35][CH:34]=2)=[CH:29][CH:28]=1>>[CH2:19]([O:18][C:4]1[CH:3]=[C:2]([NH:1][CH2:39][C:36]2[CH:35]=[CH:34][C:33]([C:30]3[CH:31]=[CH:32][C:27]([Br:26])=[CH:28][CH:29]=3)=[CH:38][CH:37]=2)[CH:17]=[CH:16][C:5]=1[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

反応物 2

HCID 13928194'-Bromo-[1,1'-biphenyl]-4-carbaldehyde

HCID 66728439Benzyl 4-Amino-2-(Benzyloxy)Benzoate

生成物 1

HCID 86694676Benzyl 2-(Benzyloxy)-4-(((4'-Bromo-[1,1'-Biphenyl]-4-Yl)Methyl)Amino)Benzoate収率 70%

実験手順

Primary aniline 1 was coupled to 4′-bromo-[1,1′-biphenyl]-4-carbaldehyde on a 3.7 mmol scale via General Procedure A to furnish 5 (1.52 g, 70%): δH (400 MHz, CDCl3) 4.39 (s, 2H, CH2), 4.59 (br s, 1H, NH), 5.10 (s, 2H, CH2), 5.31 (s, 2H, CH2), 6.20 (d, J=2.0 Hz, 1H, CH), 6.24 (d of d, J=8.6 and 2.0 Hz, 1H, CH), 7.25-7.36 (m, 6H, CH), 7.37-7.49 (m, 8H, CH), 7.53 (d, J=8.4 Hz, 2H, CH), 7.57 (d, J=8.4 Hz, 2H, CH) 7.85 (d, J=8.6 Hz, 1H, CH); δC (100 MHz, CDCl3) 47.3, 65.7, 70.3, 97.4, 104.9, 108.7, 121.5, 126.8, 127.1, 127.5, 127.6, 127.8, 127.9, 128.3, 128.3, 128.5, 131.8, 134.3, 136.6, 136.7, 137.6, 139.1, 139.4, 152.6, 160.8, 165.6.

出典と根拠

ORDレコード: ord-3b94fe1c01fd43a194e6d5a9a142da9e
出典データセット: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08846707B2

反応ノート

読み込み中…