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Potassium Carbonate → HCID 178518236, 화합물

HRID 347572
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HRID 347572 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].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]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 2763594Methyl 4-bromo-1H-pyrrole-2-carboxylateHCID 210816614-(4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholineHCID 178518234HCID 178518234, 화합물

생성물 1

HCID 178518236HCID 178518236, 화합물수율 82%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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)+.

후처리

  1. customThe reaction mixture was purged with N2 for 10 min
  2. temperatureAfter cooling
  3. additionthe mixture was diluted with H2O
  4. filtrationfiltered
  5. customto afford the crude product, which
  6. customwas triturated with DCM

출처 및 근거

ORD 기록
ord-35ab08ae1c134f45892ab64b6dd1a15f
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07173031B2

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