3-Pyridinylboronic acid → HCID 178518235, compound

HRID 2117118Notes

Reaction equation

HRID 2117118 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].Br[C:13]1[CH:14]=[C:15]([C:18](OC)=O)[NH:16][CH:17]=1.N1C=CC=C(B(O)O)C=1>CN(C=O)C.C([O-])([O-])=O.[K+].[K+].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>[N:16]1[CH:17]=[CH:13][CH:14]=[C:18]([C:2]2[CH:3]=[C:4]3[N:9]([CH:10]=2)[N:8]=[CH:7][N:6]=[C:5]3[OH:11])[CH:15]=1

Participants

7

Reactant 3

HCID 27343783-Pyridinylboronic acidHCID 2763594Methyl 4-bromo-1H-pyrrole-2-carboxylateHCID 178518234HCID 178518234, compound

Product 1

HCID 178518235HCID 178518235, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
120 °C

Procedure

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 pyridin-3-ylboronic acid (172 mg, 1.40 mmol) in 2 mL of DMF and 2 mL of saturated aqueous K2CO3 was degassed and then Pd(PPh3)4 (57 mg, 0.05 mmol) was added. The mixture was then heated to 120° C. for 3 h. LC-MS analysis indicated the disappearance of starting material. The mixture was cooled down and the solution was filtered. The filtrate was purified on preparative HPLC to afford the title compound (100 mg, 65%) as a TFA salt. MS(ESI+) m/z 213.2 (M+H)+.

Workup

  1. temperatureThe mixture was cooled down
  2. filtrationthe solution was filtered
  3. customThe filtrate was purified on preparative HPLC

Sources & evidence

ORD record
ord-7f5d443476124f54ad7333534ff1953f
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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