Potassium Carbonate → (4-{4-[5-(1-Methyl-1H-pyrazol-3-ylamino)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

HRID 76062Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]2[CH:13]=[CH:12][N:11]([CH3:14])[N:10]=2)=[CH:4][CH:3]=1.[CH3:15][O:16][C:17](=[O:40])[CH2:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:30]=[CH:29][C:28](B3OC(C)(C)C(C)(C)O3)=[CH:27][CH:26]=2)[CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH3:15][O:16][C:17](=[O:40])[CH2:18][CH:19]1[CH2:20][CH2:21][CH:22]([C:25]2[CH:26]=[CH:27][C:28]([C:2]3[CH:3]=[CH:4][C:5]([NH:8][C:9]4[CH:13]=[CH:12][N:11]([CH3:14])[N:10]=4)=[CH:6][N:7]=3)=[CH:29][CH:30]=2)[CH2:23][CH2:24]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (6-bromopyridin-3-yl)-(1-methyl-1H-pyrazol-3-yl)-amine (0.15 g, 0.6 mmol, 1.0 equiv) and {4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester (0.23 g, 0.7 mmol, 1.1 equiv) in 5 Ml DME was added 0.5 Ml saturated potassium carbonate solution followed by 5 mg Pd(PPh3)4 catalyst. The reaction was then heated to 80° C. for 2 h. Removal of volatiles in vacuo followed by silica gel chromatography (20% EtOAc in hexanes) afforded the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.14-1.26 (m, 2H) 1.54 (qd, J=12.59, 2.40 Hz, 2H) 1.68 (br. S., 1H) 1.87 (d, J=11.12 Hz, 5H) 2.31 (d, J=6.57 Hz, 2H) 3.66 (s, 3H) 3.82 (s, 3H) 5.86 (s, 1H) 7.33 (d, J=8.34 Hz, 2H) 7.59 (d, J=2.02 Hz, 1H) 7.80 (d, J=8.84 Hz, 1H) 7.93 (d, J=8.34 Hz, 2H) 7.97 (dd, J=8.84, 2.78 Hz, 1H) 8.65 (d, J=2.27 Hz, 1H) 8.83 (s, 1H); (M+H)+405.2.

Workup

customRemoval of volatiles in vacuo

Sources & evidence

ORD record: ord-ec0b5f49cdcb4cda8c3aba974a337482
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835451B2

Reaction notes

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