2-Fluorophenylboronic acid → HCID 53482544, compound

HRID 2089339Notes

Reaction equation

HRID 2089339 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH3:21])[C:6]=1[N:7]1[CH2:11][CH2:10][C@@H:9]([CH2:12][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[CH2:11][CH2:10][C@@H:9]([CH2:12][NH2:13])[CH2:8]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 58464892HCID 58464892, compound

Product 1

HCID 53482544HCID 53482544, compoundYield 48%

Procedure

Following the procedures for Example 141, (S)-tert-butyl (1-(4-amino-1-methyl-1H-pyrazol-5-yl)pyrrolidin-3-yl)methylcarbamate 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 134 as a white solid (76 mg, 48%) over three steps. 1H NMR (400 MHz, DMSO) δ 9.75 (s, 1H), 8.05 (t, J=7.9, 1H), 7.73 (dd, J=8.7, 2.0, 1H), 7.57 (s, 1H), 7.49-7.22 (m, 4H), 7.07 (s, 2H), 3.65 (s, 3H), 3.33-3.18 (m, 4H), 3.00 (dd, J=8.8, 6.3, 2H), 2.23 (dt, J=13.9, 7.0, 1H), 1.97 (td, J=12.5, 7.1, 1H), 1.68-1.55 (m, 1H). ESIMS m/z=410.1 (M+1)

Sources & evidence

ORD record
ord-f12a8cf532cc4b94a7239c654d177751
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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