Ethyl 5-bromopyridine-3-carboxylate → HCID 11236071, compound

HRID 2374954Notes

Reaction equation

HRID 2374954 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([NH2:11])=[N:6]2.Br[C:23]1[CH:24]=[N:25][CH:26]=[C:27]([CH:33]=1)[C:28]([O:30][CH2:31][CH3:32])=[O:29].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC([O-])(C)C.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([NH:11][C:23]1[CH:24]=[N:25][CH:26]=[C:27]([CH:33]=1)[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:6]2

Participants

7

Reactant 4

HCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 587120012-Amino-5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin2×

Product 1

HCID 11236071HCID 11236071, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

In a similar manner as described for Example 41, 5-methyl-7-[3-(trifluoromethyl)-phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (Intermediate 45) (0.025 g, 0.09 mmol), ethyl 5-bromonicotinate (0.020 g, 0.09 mmol), Pd2(dba)3 (0.008 g, 0.01 mmol), 2-(Di-t-butylphosphino)biphenyl (0.008 g, 0.03 mmol), and NaOtBu (0.011 g, 0.11 mmol) in 1,4-dioxane (1 mL) gave ethyl 5-({5-methyl-7-[3-(trifluoromethyl)phenyl]-imidazo[5,1-f][1,2,4]triazin-2-yl}amino)nicotinate (0.020 g) as a yellow solid. 1H NMR (Acetone-d6): δ9.24 (bs, 1H), 9.22 (s, 1H), 9.08 (d, J=2.4 Hz, 1H), 8.96-8.92 (m, 2H), 8.85 (d, J=1.4 Hz, 1H), 8.75 (s, 1H), 7.91-7.86 (m, 1H), 7.83-7.74 (m, 1H), 4.41 (q, J=7.1 Hz, 2H), 2.61 (s, 3H), 1.33 (t, J=7.1 Hz, 3H). MS m/z 443 (M+1).

Sources & evidence

ORD record
ord-17e82f9a5752491eb85bce5f14d5c615
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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