tert-Butyl 3-bromobenzylcarbamate → Tert-butyl (5'-cyano-2'-methoxybiphenyl-3-ylmethyl)carbamate

HRID 1752892Notes

Reaction equation

HRID 1752892 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][C:20]=1B1OC(C)(C)C(C)(C)O1>>[C:23]([C:22]1[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[C:26]([C:2]2[CH:16]=[CH:15][CH:14]=[C:4]([CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=2)[CH:25]=1)#[N:24]

Participants

3

Reactant 2

HCID 11033439tert-Butyl 3-bromobenzylcarbamateHCID 467397344-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Product 1

HCID 86607705Tert-butyl (5'-cyano-2'-methoxybiphenyl-3-ylmethyl)carbamateYield 68%

Procedure

Proceeding as in Reference 19, but substituting tert-butyl (3-bromo-benzyl)-carbamate (0.9 g, 3.2 mmol) and 4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile (0.9 g, 3.5 mmol), gave tert-butyl (5′-cyano-2′-methoxybiphenyl-3-ylmethyl)carbamate (0.73 g, 68%) as white foam.

Sources & evidence

ORD record
ord-917a258614c940f0be0c669fb6a8291e
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

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