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

HRID 250690ノート

反応式

HRID 250690 の反応式
[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

参加物

9

反応物 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]-

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1362a0e8c585484d9cf5379e9a97e845
出典データセット
uspto-grants-2011_01
特許番号
US07863288B2

反応ノート

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