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3-Pyridinylboronic acid → HCID 178518235, 화합물

HRID 347512
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HRID 347512 반응식
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
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7

반응물 3

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

생성물 1

HCID 178518235HCID 178518235, 화합물수율 65%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매
HCID 6228
Dimethylformamide
용매
HCID 11430Potassium Carbonate용매

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온도
120 °C

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-991b10939f604009b9e1d81cbb0ecb36
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07173031B2

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