Dichloromethane → HCID 54674362, compound

HRID 2095692Notes

Reaction equation

Br[C:2]1[N:6]([CH3:7])[C:5]([CH3:8])=[N:4][CH:3]=1.[Cl:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[C:12]([O:17][CH3:18])[C:11]=1[C@H:19]([C:21]1[C:29]2[C:24](=[N:25][CH:26]=[C:27](B3OC(C)(C)C(C)(C)O3)[CH:28]=2)[NH:23][CH:22]=1)[CH3:20].C(=O)([O-])[O-].[K+].[K+].ClCCl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[Cl:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[C:12]([O:17][CH3:18])[C:11]=1[C@H:19]([C:21]1[C:29]2[C:24](=[N:25][CH:26]=[C:27]([C:2]3[N:6]([CH3:7])[C:5]([CH3:8])=[N:4][CH:3]=3)[CH:28]=2)[NH:23][CH:22]=1)[CH3:20]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 5-bromo-1,2-dimethyl-1H-imidazole (0.0183 g, 0.104 mmol), 3-[(S)-1-(2-chloro-3-fluoro-6-methoxy-phenyl)-ethyl]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (0.030 g, 0.070 mmol), potassium carbonate (0.0289 g, 0.209 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride, dichloromethane (2.84 mg, 0.00348 mmol) in previously degassed 4:1 dioxane:water (1.50 mL) was evacuated and charged with N2 (2×) and heated under microwave conditions [Biotage, 100° C., 30 min, high absorption]. The reaction mixture was purified by Gilson HPLC resulting in the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.80 (d, J=7.1 Hz, 3H), 2.58 (s, 3H), 3.47 (s, 3H), 3.67 (s, 3H), 5.12 (q, J=7.1 Hz, 1H), 6.90 (dd, J=4.3, 9.1 Hz, 1H), 7.08 (dd, J=9.0, 9.0 Hz, 1H), 7.22 (s, 1H), 7.46 (d, J=1.0 Hz, 1H), 7.56 (s, 1H), 8.18 (d, J=1.8 Hz, 1H). MS (ES+): m/z 399.12, 401.11 (76/24) [MH+]. HPLC: tR=2.77 min (polar—5 min, ZQ3).

Workup

customwater (1.50 mL) was evacuated
additioncharged with N2 (2×)
customThe reaction mixture was purified by Gilson HPLC

Sources & evidence

ORD record: ord-703b84937ff14d55ba27c71c6f0c3993
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445510B2

Reaction notes

Loading…