2-Fluorophenylboronic acid → HCID 53482486, compound

HRID 1185293Notes

Reaction equation

HRID 1185293 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH3:22])[C:6]=1[N:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([CH2:13][NH:14]C(=O)OC(C)(C)C)[CH2:8]1.[NH2:23][C:24]1[C:25]([C:31]([OH:33])=O)=[N:26][C:27](Br)=[CH:28][CH:29]=1.[F:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1B(O)O>>[NH2:23][C:24]1[C:25]([C:31]([NH:1][C:2]2[CH:3]=[N:4][N:5]([CH3:22])[C:6]=2[N:7]2[CH2:12][CH2:11][CH2:10][C@H:9]([CH2:13][NH2:14])[CH2:8]2)=[O:33])=[N:26][C:27]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[F:34])=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 27343542-Fluorophenylboronic acidHCID 454804523-Amino-6-bromopicolinic acidHCID 58464771HCID 58464771, compound

Product 1

HCID 53482486HCID 53482486, compoundYield 18%

Procedure

Following the procedures for Example 141, (R)-tert-butyl (1-(4-amino-1-methyl-1H-pyrazol-5-yl)piperidin-3-yl)methylcarbamate, 3-amino-6-bromopicolinic acid were coupled and the intermediate amide was reacted with 2-fluorophenylboronic acid under palladium catalyzed Suzuki conditions to give 129 as a white solid (33 mg, 18%) over three steps. 1H NMR (400 MHz, DMSO) δ 9.82 (s, 1H), 8.03 (dt, J=9.6, 4.8, 1H), 7.81-7.60 (m, 2H), 7.49-7.20 (m, 4H), 7.07 (s, 2H), 3.67 (s, 3H), 3.30-3.20 (m, 2H), 3.15-2.96 (m, 3H), 2.73 (dd, J=25.7, 14.9, 1H), 1.92-1.44 (m, 4H), 1.03 (dd, J=21.1, 10.1, 1H). ESIMS m/z=424.1 (M+1)

Sources & evidence

ORD record
ord-7c694e1daaad49eca9ca44af754a2652
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

Loading…