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Bromide ion → N-phenyl-1H-pyrrolo[2,3-b]pyridin-6-amine

HRID 1261147
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HRID 1261147 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:9]1[N:14]=[C:13]2[N:15]([Si](C(C)C)(C(C)C)C(C)C)[CH:16]=[CH:17][C:12]2=[CH:11][CH:10]=1.[Br-].C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.CC([O-])(C)C.[Na+].C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:2]1([NH:1][C:9]2[N:14]=[C:13]3[NH:15][CH:16]=[CH:17][C:12]3=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 6

HCID 259Bromide ionHCID 6115AnilineHCID 6422Trifluoroacetic acidHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 580876901H-Pyrrolo[2,3-b]pyridine, 6-bromo-1-[tris(1-methylethyl)silyl]-

생성물 1

HCID 58087605
N-phenyl-1H-pyrrolo[2,3-b]pyridin-6-amine

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매2회

실험 절차

A 1 dram vial was charged with aniline (2-3 equiv), and 0.200 mL of the 588 stock solution of bromide in toluene was added. A catalyst stock solution containing 3 mmol Pd(OAc)2, 3 mmol biphenyl-2-yl-di-tert-butyl-phosphane and 15 mL of toluene was prepared and 0.050 mL of the catalyst solution was added to the reaction. An excess of NaOtBu was added as a solid to the reaction. The vial was placed in an 80° C. oven for 60 minutes (shaken several times over the hour). After cooling, the reaction was neutralized with 0.100 mL of TFA. After 30 minutes the sample was evaporated and resolvated in 0.300 mL of DMSO. The desired compound was isolated by preparative HPLC/MS. MS (ESI) [M+H+]+=210.4.

후처리

  1. additionwas added
  2. customwas prepared
  3. customwas placed in an 80° C.
  4. customfor 60 minutes
  5. temperatureAfter cooling
  6. customAfter 30 minutes the sample was evaporated

출처 및 근거

ORD 기록
ord-26bc05cdba7f44528735906ec66f0ade
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08470818B2

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