2-Fluorophenylboronic acid → HCID 53482384, compound

HRID 1185287Notes

Reaction equation

HRID 1185287 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH3:21])[C:6]=1[O:7][CH:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1.[NH2:22][C:23]1[C:24]([C:30]([OH:32])=O)=[N:25][C:26](Br)=[CH:27][CH:28]=1.[F:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1B(O)O>>[NH2:22][C:23]1[C:24]([C:30]([NH:1][C:2]2[CH:3]=[N:4][N:5]([CH3:21])[C:6]=2[O:7][CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[O:32])=[N:25][C:26]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[F:33])=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 27343542-Fluorophenylboronic acidHCID 454804523-Amino-6-bromopicolinic acidHCID 67437186HCID 67437186, compound

Product 1

HCID 53482384HCID 53482384, compoundYield 14%

Procedure

Following the procedures for Example 141, tert-butyl 4-(4-amino-1-methyl-1H-pyrazol-5-yloxy)piperidine-1-carboxylate and 3-amino-6-bromopicolinic acid were coupled and the intermediate amide was reacted with 2-fluorophenylboronic acid under palladium catalyzed Suzuki conditions to give 116 as a white solid (10 mg, 14%) over three steps. 1H NMR (400 MHz, DMSO) δ 9.67 (s, 1H), 8.05 (t, J=7.5, 1H), 7.73 (dd, J=8.8, 1.9, 1H), 7.66-7.38 (m, 3H), 7.38-7.25 (m, 3H), 7.03 (s, 2H), 4.43-4.20 (m, 1H), 3.63 (s, 3H), 2.96-2.79 (m, 2H), 2.39 (dd, J=26.9, 16.6, 2H), 1.92 (d, J=12.0, 2H), 1.55 (td, J=13.2, 3.9, 2H). ESIMS m/z=411.1 (M+1)

Sources & evidence

ORD record
ord-3d8d125b98444640909050a32519080f
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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