Nitrogen → HCID 66716967, compound

HRID 2409594Notes

Reaction equation

Br[C:2]1[S:6][C:5]2=[N:7][CH:8]=[CH:9][N:4]2[N:3]=1.[F:10][C:11]([F:29])([F:28])[C:12]1[C:13]([NH2:27])=[N:14][CH:15]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:17]=1.C([O-])([O-])=O.[K+].[K+].N#N>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[F:29][C:11]([F:10])([F:28])[C:12]1[C:13]([NH2:27])=[N:14][CH:15]=[C:16]([C:2]2[S:6][C:5]3=[N:7][CH:8]=[CH:9][N:4]3[N:3]=2)[CH:17]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of 2-bromo-imidazo[2,1-b][1,3,4]thiadiazole (0.469 g, 2.3 mmol, 1 eq), 3-(trifluoromethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (1.7 g, 3.5 mmol, 1.5 eq), dioxane (8 mL) and a sat. aq. solution of K2CO3 (1 mL) was degassed (N2, 5 min) at RT. Pd(Ph3P)2Cl2 (0.404 g, 0.250 mmol, 1 eq) was added, and the reaction mixture was heated at 110° C. under N2 for 2 h. The solvent was evaporated, and the residue was taken up in AcOEt and n-BuOH and washed with water. The organic phase was separated, dried (Na2SO4), filtered and concentrated. The residue was treated with MeOH, filtered off and dried to give the desired product (0.244 g, 37%). HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=3.61 min, [M+H]+ m/z 286.0.

Workup

customThe solvent was evaporated
washn-BuOH and washed with water
customThe organic phase was separated
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
additionThe residue was treated with MeOH
filtrationfiltered off
customdried

Sources & evidence

ORD record: ord-ad872fe5a7374072ad3c89b1e0145720
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815918B2

Reaction notes

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