Furan-3-boronic acid → 2-Amino-6-(furan-3-yl)benzonitrile

HRID 711908Notes

Reaction equation

HRID 711908 reaction equation
[O:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.[NH2:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14](Br)[C:11]=1[C:12]#[N:13]>>[NH2:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)[C:11]=1[C:12]#[N:13]

Participants

3

Reactant 2

HCID 2734358Furan-3-boronic acidHCID 98130382-Amino-6-bromobenzonitrile

Product 1

HCID 673988752-Amino-6-(furan-3-yl)benzonitrileYield 74%

Procedure

Prepared as in Example 129c from furan-3-ylboronic acid and 2-amino-6-bromobenzonitrile in 74% yield as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 4.51 (br s, 2H), 6.66 (dd, J=1.2, 8.4 Hz, 1H), 6.78 (dd, J=1.2, 2.0 Hz, 1H), 6.82 (dd, J=1.2, 8.0 Hz, 1H), 7.31 (t, J=8.0 Hz, 1H), 7.50 (t, J=1.6 Hz, 1H), 7.95 (dd, J=1.2, 1.6 Hz, 1H).

Sources & evidence

ORD record
ord-839c526c791c49a39c459284f6a35100
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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