2-Fluorophenylboronic acid → HCID 53482668, compound

HRID 1185302Notes

Reaction equation

HRID 1185302 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH3:21])[C:6]=1[N:7]1[CH2:12][CH:11]2[CH:9]([CH:10]2[NH:13]C(=O)OC(C)(C)C)[CH2:8]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[N:7]2[CH2:8][CH:9]3[CH:11]([CH:10]3[NH2:13])[CH2:12]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 58465028HCID 58465028, compound

Product 1

HCID 53482668HCID 53482668, compoundYield 35%

Procedure

Following the procedures for Example 141, tert-butyl 3-(4-amino-1-methyl-1H-pyrazol-5-yl)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate 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 151 as a white solid (32 mg, 35%) over three steps. 1H NMR (400 MHz, DMSO) δ 9.69 (s, 1H), 8.06 (t, J=7.8, 1H), 7.75 (d, J=8.5, 1H), 7.66-7.25 (m, 5H), 7.06 (s, 2H), 3.59 (s, 3H), 3.40 (t, J=10.6, 2H), 3.17 (d, J=8.5, 2H), 2.09 (s, 1H), 1.44 (s, 2H). ESIMS m/z=408.1 (M+1)

Sources & evidence

ORD record
ord-24bffce9d4824796a4d63b30d5433399
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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