4-Fluorophenylboronic acid → HCID 71138676, compound

HRID 1506595Notes

Reaction equation

HRID 1506595 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:34])([CH2:28][N:29]1[CH:33]=[N:32][N:31]=[N:30]1)[C:10]([C:13]1[N:18]=[CH:17][C:16]([O:19][C:20]2[CH:27]=[CH:26][C:23](C#N)=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)([F:12])[F:11].[F:35]C1C=CC(B(O)O)=CC=1>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:34])([CH2:28][N:29]1[CH:33]=[N:32][N:31]=[N:30]1)[C:10]([F:11])([F:12])[C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]2[CH:21]=[CH:22][C:23]([F:35])=[CH:26][CH:27]=2)=[CH:17][N:18]=1

Participants

3

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 71138867HCID 71138867, compound

Product 1

HCID 71138676HCID 71138676, compoundYield 42.4%

Procedure

Compound 6 was prepared in a similar manner to compound 5 from (4-fluorophenyl)boronic acid to afford a solid 6 (0.1 g, 0.22 mmol, 42.4%). 1H NMR (500 MHz, CDCl3): δ 8.73 (s, 1H), 8.20 (d, J=2.5 Hz, 1H), 7.53 (d, J=9.0 Hz, 1H), 7.43-7.38 (m, 2H), 7.27 (d, J=2.5 Hz, 1H), 7.26-7.03 (m, 4H), 6.79-6.70 (m, 2H), 5.49 (d, J=14.5 Hz, 1H), 5.15 (d, J=14.5 Hz, 1H). MS (ESI): m/z 494.1 [M++1]. HPLC: 99.43%.

Sources & evidence

ORD record
ord-70cf23115ea941df9b5eeb5a60876bab
Source dataset
uspto-grants-2015_12
Patent number
US09220265B2

Reaction notes

Loading…