B-(1E)-1-Hexenylboronic acid → HCID 59519555, compound

HRID 1162136Notes

Reaction equation

HRID 1162136 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][C:13]3[CH:18]=[N:17][C:16]([CH3:19])=[CH:15][N:14]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH:20](/B(O)O)=[CH:21]\[CH2:22][CH2:23][CH2:24][CH3:25]>>[CH:20](/[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][C:13]3[CH:18]=[N:17][C:16]([CH3:19])=[CH:15][N:14]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)=[CH:21]\[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

3

Reactant 2

HCID 5326225B-(1E)-1-Hexenylboronic acidHCID 68648262HCID 68648262, compound

Product 1

HCID 59519555HCID 59519555, compoundYield 40%

Procedure

Prepared from the product of step A and (E)-1-hexeneboronic acid according to general procedure 2 providing the title compound (20 mg, 40%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 8.55 (s, 1H), 8.48 (s, 1H), 7.60 (d, J=9.5 Hz, 1H), 7.39 (s, 1H), 6.75 (d, J=9.5 Hz, 1H), 6.51-6.40 (m, 2H), 4.67 (s, 2H), 2.52 (s, 3H), 2.20-2.15 (m, 2H), 1.42-1.34 (m, 4H), 0.94 (t, J=7.0 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 154.8, 153.4, 153.1, 144.9, 143.4, 137.9, 133.2, 129.3, 128.6, 126.0, 116.6, 113.1, 45.9, 34.4, 32.8, 23.4, 20.9, 14.3; HPLC tR=14.6 min (Luna), 98.1%; ES-MS: (M+H)=323 m/z.

Sources & evidence

ORD record
ord-e89e2fcd6f1c4a089431ba5acc204236
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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