Water → HCID 178491830, compound

HRID 2095629Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:10]([C@@H:11]([C:13]3[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]([F:21])[C:14]=3[Cl:22])[CH3:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:23][C:24]1[C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][NH:26][N:25]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[Cl:22][C:14]1[C:15]([F:21])=[CH:16][CH:17]=[C:18]([O:19][CH3:20])[C:13]=1[C@H:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:28]3[C:24]([CH3:23])=[N:25][NH:26][CH:27]=3)[CH:3]=2)[NH:8][CH:9]=1)[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-Bromo-3-[(S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (12 mg, 0.031 mmol), 3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (13.0 mg, 0.0626 mmol), potassium carbonate (0.0130 g, 0.0938 mmol) and 4:1 Dioxane:water (4:1,1,4-Dioxane:H2O, 0.31 mL, 3.1 mmol) were added to a microwave vessel and the vessel was degassed 3×. The reaction was heated in the microwave at 100° C. for 30 min. Reaction mixture was concentrated in vacuo and purified by HPLC to afford the title compound. 1H NMR (400 MHz, CD3OD): δ=1.82 (d, J=7.3 Hz, 3H), 2.23 (s, 3H), 3.66 (br. s., 3H), 5.12 (d, J=6.8 Hz, 1H), 6.91 (dd, J=9.0, 4.2 Hz, 1H), 7.10 (t, J=9.0 Hz, 1H), 7.36 (d, J=1.3 Hz, 1H), 7.48 (s, 1H), 7.62 (br. s., 1H), 8.18 (d, J=1.8 Hz, 1H). MS (ES+): m/z=384.96/386.94 (100/65) [MH+]. HPLC: tR=3.19 min (ZQ3, polar—5 min).

Workup

customthe vessel was degassed 3×
customReaction mixture
concentrationwas concentrated in vacuo
custompurified by HPLC

Sources & evidence

ORD record: ord-9c0d313251914a689a3a290fe3218817
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445510B2

Reaction notes

Loading…