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

HRID 2069940Notes

Reaction equation

HRID 2069940 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[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:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:10]=[C:11]([C:20]2[CH:21]=[C:22]([C:23]#[N:24])[CH:25]=[CH:26][C:19]=2[O:18][CH3:17])[CH:12]=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2]

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-a9240e7257b14c3dba3366289f6bc45e
Source dataset
uspto-grants-2012_10
Patent number
US08299110B2

Reaction notes

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