Sodium Carbonate → HCID 66615848, compound

HRID 1404256Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]2[CH:10]=[N:11][C:12]([O:16][CH3:17])=[C:13]([F:15])[CH:14]=2)=[CH:4][CH:3]=1.[CH3:18][O:19][C:20](=[O:43])[CH2:21][CH:22]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:33]=[CH:32][C:31](B3OC(C)(C)C(C)(C)O3)=[CH:30][CH:29]=2)[CH2:24][CH2:23]1.C(=O)([O-])[O-].[Na+].[Na+]>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>[CH3:18][O:19][C:20](=[O:43])[CH2:21][CH:22]1[CH2:23][CH2:24][CH:25]([C:28]2[CH:29]=[CH:30][C:31]([C:2]3[CH:3]=[CH:4][C:5]([NH:8][C:9]4[CH:10]=[N:11][C:12]([O:16][CH3:17])=[C:13]([F:15])[CH:14]=4)=[CH:6][N:7]=3)=[CH:32][CH:33]=2)[CH2:26][CH2:27]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (6-bromo-pyridin-3-yl)-(5-fluoro-6-methoxy-pyridin-3-yl)-amine (0.17 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 (0.22 g, 0.6 mmol, 1.0 equiv) in 15 Ml DME was added 1 Ml saturated sodium carbonate solution followed by 10 mg Pd(PPh3)4 catalyst. The reaction was then heated to 80° C. overnight. 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 0.93-1.08 (m, 1 H) 1.01 (d, J=2.78 Hz, 1 H) 1.31-1.52 (m, 3. H) 1.62 (s, 2 H) 1.69 (d, J=9.85 Hz, 4 H) 2.02 (d, J=7.07 Hz, 2 H) 3.81 (s, 3 H) 7.28 (d, J=8.34 Hz, 2 H) 7.58 (d, J=13.89 Hz, 1 H) 7.75 (d, J=8.34 Hz, 3 H) 7.70 (d, J=8.59 Hz, 1 H) 7.81 (d, J=2.27 Hz, 1 H) 7.89 (d, J=8.84 Hz, 1 H) 8.15 (s, 1 H) 9.04 (br. S., 1 H); (M+H)+ 450.3.

Workup

customRemoval of volatiles in vacuo

Sources & evidence

ORD record: ord-07f876d7b0034d348b3e1e9f59c2e8e2
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912208B2

Reaction notes

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