1,4-Dioxane → HCID 89510077, compound

HRID 1844582Notes

Reaction equation

C(OC([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[CH:10]=[C:9]1B(O)O)=O)(C)(C)C.Br[C:21]1[CH:22]=[C:23]([O:32][CH3:33])[C:24](=[CH:26]N(CC)CC)[N:25]=1.[O-:34]P([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>O.CCO>[CH3:33][O:32][C:23]1[CH:22]=[C:21]([C:9]2[NH:8][C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)[NH:25][C:24]=1[CH:26]=[O:34]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-(tert-butoxycarbonyl)-1H-pyrrolo[2,3-b]pyridin-2-ylboronic acid (150 mg, 0.57 mmol), N-((5-bromo-3-methoxy-2H-pyrrol-2-ylidene)methyl)-N-ethylethanamine (114 mg, 0.44 mmol, provided by Chemzon Scientific Inc, Montreal, Canada), Pd(dppf)2Cl2CH2Cl2 (16 mg, 0.02 mmol) and K3PO4 (187 mg, 0.88 mmol) in a 20 mL sealed-tube flask was vented 4 times with nitrogen. 1,4-Dioxane (2.2 mL) and water (0.3 mL) were introduced by syringe and the mixture was vented twice with nitrogen. The reaction mixture was then heated at 80° C. for 2 h and TLC showed no starting materials were left. EtOH (15 mL) and water (5 mL) were added and the reaction mixture was stirred for 0.5 h at r.t. and then extracted with 2×15 mL of EtOAc. The extracts were dried over Na2SO4, filtered through a pad of silica gel. The filtrate was concentrated under vacuum to give 15 mg of the title compound as a dark solid.

Workup

waitwere left
extractionextracted with 2×15 mL of EtOAc
dry with materialThe extracts were dried over Na2SO4
filtrationfiltered through a pad of silica gel
concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record: ord-52d2083fca5b4c138f24817bb9dbd1f8
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946445B2

Reaction notes

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