B-(1E)-1-Hexenylboronic acid → HCID 59519544, compound

HRID 1162138Notes

Reaction equation

HRID 1162138 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=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:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)=[CH:20]\[CH2:21][CH2:22][CH2:23][CH3:24]

Participants

3

Reactant 2

HCID 5326225B-(1E)-1-Hexenylboronic acidHCID 68647725HCID 68647725, compound

Product 1

HCID 59519544HCID 59519544, compoundYield 50%

Procedure

Prepared from the product of step A and (E)-1-hexeneboronic acid according to general procedure 2 providing the title compound (75 mg, 50%) as a brown solid; 1H NMR (300 MHz, CD3OD) δ 8.60 (s, 1H), 8.42-8.40 (m, 1H), 7.91 (d, J=7.8 Hz, 1H), 7.57 (d, J=9.7 Hz, 1H), 7.41-7.37 (m, 2H), 6.71-6.47 (m, 3H), 4.60 (s, 2H), 2.24-2.18 (m, 2H), 1.44-1.32 (m, 4H), 0.93 (t, J=7.0 Hz, 3H); 13C NMR (75 MHz, CD3OD) δ 154.8, 149.5, 148.6, 137.9, 137.5, 137.4, 133.2, 129.1, 128.7, 125.9, 125.2, 116.7, 113.2, 43.9, 34.4, 32.8, 23.3, 14.4; HPLC tR=11.4 min (Luna), 96.0%; ES-MS: (M+H)=308 m/z.

Sources & evidence

ORD record
ord-7f00548c56734ac9bbcbab28535357ba
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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