2-Fluoro-5-(trifluoromethyl)phenylboronic acid → HCID 59612351, compound

HRID 1890026Notes

Reaction equation

HRID 1890026 reaction equation
BrC1C2N(N=C(Cl)N=2)C=CC=1.FC1C=CC(C(F)(F)F)=CC=1B(O)O.[Cl:26][C:27]1[N:43]=[C:30]2[C:31]([C:35]3[C:36]([O:41][CH3:42])=[N:37][CH:38]=[CH:39][CH:40]=3)=[CH:32][CH:33]=[CH:34][N:29]2[N:28]=1.[C:44]([O:48][C:49]([N:51]1[CH2:56][CH2:55][CH:54]([C:57]2[CH:62]=[CH:61][C:60]([NH2:63])=[CH:59][CH:58]=2)[CH2:53][CH2:52]1)=[O:50])([CH3:47])([CH3:46])[CH3:45].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[Cl:26][C:27]1[N:43]=[C:30]2[C:31]([C:35]3[C:36]([O:41][CH3:42])=[N:37][CH:38]=[CH:39][CH:40]=3)=[CH:32][CH:33]=[CH:34][N:29]2[N:28]=1.[C:44]([O:48][C:49]([N:51]1[CH2:56][CH2:55][CH:54]([C:57]2[CH:62]=[CH:61][C:60]([NH:63][C:27]3[N:43]=[C:30]4[C:31]([C:35]5[C:36]([O:41][CH3:42])=[N:37][CH:38]=[CH:39][CH:40]=5)=[CH:32][CH:33]=[CH:34][N:29]4[N:28]=3)=[CH:59][CH:58]=2)[CH2:53][CH2:52]1)=[O:50])([CH3:47])([CH3:45])[CH3:46]

Participants

7

Reactant 5

HCID 27633012-Fluoro-5-(trifluoromethyl)phenylboronic acidHCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylateHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 674813708-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridineHCID 67481470HCID 67481470, compound

Product 2

HCID 59612351HCID 59612351, compoundHCID 67481470HCID 67481470, compound

Procedure

2-Chloro-8-(2-methoxy-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine was prepared from 8-bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine and 2-fluoro-5-trifluoromethylphenylboronic acid in a manner analogous to Example 2c (0.47 g, 84%). MP=218-219° C. MS=261 (MH)+. 271b) [4-{4-[8-(2-Methoxy-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester was prepared from 2-Chloro-8-(2-methoxy-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine and 4-(4-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester with 2,2′-bis-dicyclohexylphosphanyl-biphenyl as the ligand in a manner analogous to Example 2d (0.25 g, 50%). MP=101-103° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.75 (s, 1H), 8.80 (d, J=6.58 Hz, 1H), 8.25 (m, 1H), 8.05 (d, 1H), 7.75 (m, 1H), 7.55 (m, 2H), 7.02 (m, 4H), 4.05 (m, 2H), 3.90 (s, 3H), 2.6-2.8 (m, 3H), 1.65 (m, 2H), 1.40 (m, 11H). MS=501 (MH)+.

Sources & evidence

ORD record
ord-c5c8431595094083b080e2b68c03b56b
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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