Potassium Carbonate → HCID 178518236, compound
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[N:8]=[CH:7][N:6]=[C:5]2[OH:11].BrC1C=C(C(OC)=O)NC=1.CC1(C)C(C)(C)OB([C:30]2[CH:35]=[CH:34][N:33]=[C:32]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[CH:31]=2)O1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:39]1[CH2:40][CH2:41][N:36]([C:32]2[CH:31]=[C:30]([C:2]3[CH:3]=[C:4]4[N:9]([CH:10]=3)[N:8]=[CH:7][N:6]=[C:5]4[OH:11])[CH:35]=[CH:34][N:33]=2)[CH2:37][CH2:38]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 6-bromopyrrolo[2,1-f][1,2,4]triazin-4-ol (100 mg, 0.47 mmol, prepared from methyl 4-bromo-1H-pyrrole-2-carboxylate: see, generally, Kitamura, C. and Yamashita, Y. J. Chem. Soc. Perkin Trans. 1, 1997, 1443, the disclosure of which is herein incorporated by reference, using a similar procedure outlined in the PCT Appl. WO 00/71129) and 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine (290 mg, 1.0 mmol) in DMF (2 mL) were added saturated aq. K2CO3 solution (2.0 mL) and Pd(PPh3)4 (60 mg, 0.05 mmol). The reaction mixture was purged with N2 for 10 min and then was heated at 80° C. for 5 h and 100° C. for 12 h. After cooling, the mixture was diluted with H2O and filtered to afford the crude product, which was triturated with DCM to provide the title compound (114 mg, 82% yield). MS(ESI) m/z 298.2 (M+H)+.
Workup
- customThe reaction mixture was purged with N2 for 10 min
- temperatureAfter cooling
- additionthe mixture was diluted with H2O
- filtrationfiltered
- customto afford the crude product, which
- customwas triturated with DCM
Sources & evidence
- ORD record
- ord-35ab08ae1c134f45892ab64b6dd1a15f
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07173031B2
Reaction notes
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