4'-Bromo-[1,1'-biphenyl]-4-carbaldehyde → HCID 86694676, compound

HRID 81860Notes

Reaction equation

HRID 81860 reaction equation
[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

Participants

3

Reactant 2

HCID 13928194'-Bromo-[1,1'-biphenyl]-4-carbaldehydeHCID 66728439Benzyl 4-Amino-2-(Benzyloxy)Benzoate

Product 1

HCID 86694676HCID 86694676, compoundYield 70%

Procedure

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.

Sources & evidence

ORD record
ord-3b94fe1c01fd43a194e6d5a9a142da9e
Source dataset
uspto-grants-2014_09
Patent number
US08846707B2

Reaction notes

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