Sodium Carbonate → 4-{2-Methyl-5-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-thiazol-2-ylamine

HRID 85093Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:12]=[C:13]([NH2:16])[S:14][CH:15]=3)=[C:9]([CH3:17])[NH:8][C:5]2=[N:6][CH:7]=1.[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:27]=2)[CH2:21][CH2:20]1.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C.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>[CH3:17][C:9]1[NH:8][C:5]2=[N:6][CH:7]=[C:2]([C:29]3[CH:28]=[CH:27][C:26]([CH2:25][N:22]4[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]4)=[CH:31][CH:30]=3)[CH:3]=[C:4]2[C:10]=1[C:11]1[N:12]=[C:13]([NH2:16])[S:14][CH:15]=1

Participants

Conditions

Temperature: 175 °C

Procedure

In a personal chemistry microwave reaction vial 4-(5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-ylamine (0.2 g, 0.64 mmol) and 1-Methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-piperazine (0.23 g, 0.71 mmol), bis(triphenylphosphine)-palladium(II) dichloride (0.004 g, 0.006 mmol) in acetonitrile (2 mL), and 1 M Na2CO3 (2 mL) were added. The resulting mixture was de-gassed with N2 for 10 min, after which it was heated at 175° C. for 30 min in a Personal Chemistry Optimizer. The mixture was diluted with DMF (3 mL), and concentrated in vacuo and purified on silica gel column using dichloromethane and methanol to afford 4-{2-Methyl-5-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-thiazol-2-ylamine.

Workup

additionwere added
customThe resulting mixture was de-gassed with N2 for 10 min
additionThe mixture was diluted with DMF (3 mL)
concentrationconcentrated in vacuo
custompurified on silica gel column

Sources & evidence

ORD record: ord-e1aedcd281ce4b508a5f5a2471061f49
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846909B2

Reaction notes

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