4-[4-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-phenyl]-butyric acid → (3-Cyanophenyl)carbamic acid 2-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-phenyl]ethyl ester

HRID 735517Notes

Reaction equation

HRID 735517 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][O:6][B:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15]CC(O)=O)=[CH:10][CH:9]=2)[O:4][CH2:3]1.BrC1C=CC(CC[O:30][C:31](=[O:41])[NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]#[N:40])[CH:34]=2)=CC=1>>[CH3:20][C:2]1([CH3:1])[CH2:3][O:4][B:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][O:41][C:31](=[O:30])[NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([C:39]#[N:40])[CH:34]=3)=[CH:12][CH:13]=2)[O:6][CH2:7]1

Participants

3

Reactant 2

HCID 578427774-[4-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-phenyl]-butyric acidHCID 578428264-Bromophenethyl 3-cyanophenylcarbamate

Product 1

HCID 57842566(3-Cyanophenyl)carbamic acid 2-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-phenyl]ethyl esterYield 76%

Procedure

Using a procedure analogous to that used to prepare 2A, 11A (516 mg, 1.50 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 11B (434 mg, 76%). This crude material was taken on to the next step.

Sources & evidence

ORD record
ord-5a0817db0c864938b1ebd96e8c03336b
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…