B-(1E)-1-Hexenylboronic acid → HCID 59519549, compound

HRID 1162134Notes

Reaction equation

Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH:19](/B(O)O)=[CH:20]\[CH2:21][CH2:22][CH2:23][CH3:24]>>[CH:19](/[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)=[CH:20]\[CH2:21][CH2:22][CH2:23][CH3:24]

Participants

Reactant 2

HCID 5326225B-(1E)-1-Hexenylboronic acid

HCID 68648294HCID 68648294, compound

Product 1

HCID 59519549HCID 59519549, compoundYield 53%

Procedure

Prepared from the product of step A and (E)-1-hexeneboronic acid according to general procedure 2 providing the title compound (47 mg, 53%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 8.46-8.44 (m, 2H), 7.61 (d, J=9.1 Hz, 1H), 7.46 (d, J=7.1 Hz, 2H), 7.38 (s, 1H), 6.75 (d, J=9.7 Hz, 1H), 6.56-6.37 (m, 2H), 4.62 (s, 2H), 2.18-2.11 (q, J=6.5 Hz, 2H), 1.39-1.28 (m, 4H), 0.92 (t, J=7.1 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 154.8, 152.0, 150.0, 138.0, 133.1, 129.4, 128.6, 125.9, 123.9, 116.6, 113.0, 45.5, 34.3, 32.7, 23.3, 14.3; HPLC tR=10.9 min (Luna), 97.4%; ES-MS: (M+H)=308 m/z.

Sources & evidence

ORD record: ord-21f7227aee63443483be0ccb49fdd8d4
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820670B2

Reaction notes

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