6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-amine → HCID 86669093, compound

HRID 1520954Notes

Reaction equation

HRID 1520954 reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][CH2:4][C:5]([C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1)=O.[F:20][C:21]([F:35])([F:34])[C:22]1[CH:23]=[N:24][N:25]([C:27]2[N:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=2)[CH:26]=1.[B][B][B][B][B][B][B][B][B][B]>CO>[F:1][C:2]([F:19])([F:18])[CH2:3][CH2:4][CH:5]([C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1)[NH:33][C:30]1[CH:31]=[N:32][C:27]([N:25]2[CH:26]=[C:22]([C:21]([F:35])([F:34])[F:20])[CH:23]=[N:24]2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 641732966-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-amineHCID 68157804Ethyl 4-(4,4,4-trifluorobutanoyl)benzoateHCID 178419135HCID 178419135, compound

Product 1

HCID 86669093HCID 86669093, compoundYield 43,921%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude ethyl 4-(4,4,4-trifluorobutanoyl)benzoate (0.060 g, 0.22 mmol) and 6-[4-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-3-amine (0.050 g, 0.22 mmol) in methanol (2.2 ml) was added decaborane (8.0 mg, 0.066 mmol). The reaction was stirred for 12 hours at ambient temperature. The reaction mixture was quenched with aqueous 1.0M hydrochloric acid and concentrated in vacuo. The crude material was purified via ISCO MPLC (SiO2, 0-100% ethyl acetate in heptane) to yield the product (47 g, 42%) as an oil. 1H NMR (400 MHz, CDCl3): δ 8.63 (s, 1H), 8.06 (d, J=8.4 Hz, 2H), 7.80 (s, 1H), 7.75 (d, J=2.5 Hz, 1H), 7.70 (d, J=8.8 Hz, 1H), 7.38-7.45 (m, 2H), 6.96 (dd, J=8.8, 2.7 Hz, 1H), 4.50 (t, J=6.2 Hz, 1H), 4.37 (q, J=7.0 Hz, 2H), 2.07-2.32 (m, 4H), 1.39 (t, J=7.2 Hz, 3H). MS (M+1): 487.3.

Workup

  1. customThe reaction mixture was quenched with aqueous 1.0M hydrochloric acid
  2. concentrationconcentrated in vacuo
  3. customThe crude material was purified via ISCO MPLC (SiO2, 0-100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-6af0c65b1551411197dbfef2b02e843b
Source dataset
uspto-grants-2015_07
Patent number
US09073871B2

Reaction notes

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