Diisopropylethylamine → 2-fluoro-N-methyl-4-[3-(quinolin-6-ylthio)imidazo[1,2-a]pyrimidin-6-yl]benzamide

HRID 500130Notes

Reaction equation

C(N(CC)C(C)C)(C)C.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.Br[C:53]1[N:57]2[CH:58]=[C:59]([C:62]3[CH:71]=[CH:70][C:65]([C:66]([NH:68][CH3:69])=[O:67])=[C:64]([F:72])[CH:63]=3)[CH:60]=[N:61][C:56]2=[N:55][CH:54]=1.[N:73]1[C:82]2[C:77](=[CH:78][C:79]([SH:83])=[CH:80][CH:81]=2)[CH:76]=[CH:75][CH:74]=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:72][C:64]1[CH:63]=[C:62]([C:59]2[CH:60]=[N:61][C:56]3[N:57]([C:53]([S:83][C:79]4[CH:78]=[C:77]5[C:82](=[CH:81][CH:80]=4)[N:73]=[CH:74][CH:75]=[CH:76]5)=[CH:54][N:55]=3)[CH:58]=2)[CH:71]=[CH:70][C:65]=1[C:66]([NH:68][CH3:69])=[O:67]

Participants

Conditions

Temperature: 100 °C

Procedure

N,N-Diisopropylethylamine (70 μL, 0.4 mmol), tris(dibenzylideneacetone)-dipalladium(0) (4.58 mg, 0.0050 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (5.79 mg, 0.010 mmol) was added successively to a solution of 4-(3-bromoimidazo[1,2-a]pyrimidin-6-yl)-2-fluoro-N-methylbenzamide (69.8 mg, 0.2 mmol) and quinoline-6-thiol (32.2 mg, 0.2 mmol) in 1,4-dioxane (0.42 mL) in a microwave tube. The tube was sealed and degassed three times, and heated to 100° C. overnight. After cooling, the reaction mixture was diluted with methanol, and filtered. The filtrate was purified by RP-HPLC (pH 10) to give the desired product. LCMS: (M+H)=430.0.

Workup

customThe tube was sealed
customdegassed three times
temperatureAfter cooling
additionthe reaction mixture was diluted with methanol
filtrationfiltered
customThe filtrate was purified by RP-HPLC (pH 10)

Sources & evidence

ORD record: ord-fa6001e04b084f4f9dff1930c5b98b70
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

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