Potassium Carbonate → HCID 57812598, compound

HRID 912005Notes

Reaction equation

Br[C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH2:23])=[C:10]([O:11][C@@H:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([F:21])[C:15]=3[Cl:22])[CH3:13])[C:5]=2[O:4][CH:3]=1.[CH:24]([C:26]1[S:27][CH:28]=[C:29](B(O)O)[CH:30]=1)=[O:25].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O.C(Cl)Cl>[NH2:23][C:9]1[N:8]=[CH:7][C:6]2[C:2]([C:29]3[CH:30]=[C:26]([CH:24]=[O:25])[S:27][CH:28]=3)=[CH:3][O:4][C:5]=2[C:10]=1[O:11][C@@H:12]([C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([F:21])[C:15]=1[Cl:22])[CH3:13]

Participants

Conditions

Temperature: 80 °C

Procedure

3-Bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine (150.0 mg, 0.357 mmol), 2-formylthiophene-4-boronic acid (111 mg, 0.714 mmol), potassium carbonate (148 mg, 1.07 mmol), 1,4-dioxane (4.2 mL, 54 mmol), H2O (1.2 mL, 67 mmol) and (1,1′bis-(diphenylphosphino)ferrocene palladium dichloride (10 mg, 0.02 mmol) were mixed and heated at 80° C. overnight. The crude was worked up with DCM and H2O. Product was purified by prep-TLC in DCM/methanol system. MS (ES+): m/z 451.01/453.04 (100/73) [MH+]. HPLC: tR=0.93 min (HPLC-ACQUITY, Analytical). 1H NMR (400 MHz, DMSO-d6): δ 9.99 (d, J=1.3 Hz, 1H), 8.49 (s, 1H), 8.42-8.47 (m, 2H), 8.26 (s, 1H), 7.49-7.56 (m, 1H), 7.42-7.49 (m, 1H), 6.26 (q, J=6.7 Hz, 1H), 5.71 (s, 2H), 1.85 (d, J=6.8 Hz, 3H).

Workup

customProduct was purified by prep-TLC in DCM/methanol system

Sources & evidence

ORD record: ord-8ed509a205264f61b155a4e1a85a8358
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022206B2

Reaction notes

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