Water → HCID 66591283, 화합물

HRID 1092276

반응식

HRID 1092276 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.CN[C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.O.[CH3:21][N:22](C)C=O>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>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]2[CH:14]=[C:13]([CH2:21][NH2:22])[CH:12]=[CH:11][CH:16]=2)=[N:3][CH:4]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 693532,5-DibromopyridineHCID 23558980[3-(Methylamino)phenyl]boronic acid

생성물 1

HCID 66591283HCID 66591283, 화합물수율 52%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

반응 조건

온도
90 °C

실험 절차

2.2 g (9.5 mmol, 1.2 eq) of 2,5-dibromopyridine are dissolved in 3 mL of an 8/2 mixture of dimethylformamide/2M potassium phosphate. 1.2 g (7.9 mmol, 1 eq) of N-methyl-3-aminophenylboronic acid are added along with 456 mg (0.39 mmol, 5 mol %) of tetrakis(triphenylphosphine)palladium. The mixture is stirred for 3 hours at 90° C. The reaction is stopped by adding 30 mL of water and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated and the residue is then chromatographed on silica gel (80/20 to 70/30 heptane/ethyl acetate). 1.07 g of [3-(5-bromopyrid-2-yl)phenyl]methylamine are obtained. Yield 52%.

후처리

  1. extractionis then extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated
  4. customthe residue is then chromatographed on silica gel (80/20 to 70/30 heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-5462fe44302a4c3a93cb4fa2f07ab868
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129416B2

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