Water → HCID 86718003, 화합물

HRID 1500464노트

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HRID 1500464 반응식
Br[C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([NH2:11])=[CH:4][C:3]=1[CH3:12].[N:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>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>[CH3:12][C:3]1[CH:4]=[C:5]([NH2:11])[C:6]2[O:10][CH2:9][CH2:8][C:7]=2[C:2]=1[C:16]1[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=1

참가 물질

7

반응물 4

HCID 962Water2회HCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86718002HCID 86718002, 화합물

생성물 1

HCID 86718003HCID 86718003, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

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온도
135 °C

실험 절차

A mixture of 4-bromo-5-methyl-2,3-dihydrobenzofuran-7-amine (1e) (0.80 g, 3.5 mmol), pyridin-4-ylboronic acid (0.86 g, 7 mmol), Cs2CO3 (2.84 g, 8.7 mmol), Pd(PPh3)4 (0.40 g, 0.346 mmol) and water (7 mL) in DMF (35 mL) was stirred at 135° C., under N2 for 1 h. It was cooled to ambient temperature, poured into water (50 mL), extracted with EtOAc (150 mL), washed with water, brine, dried and concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1 to 5:1 to 1:1) to give the title compound (1f) as a yellow solid. MS-ESI (m/z): 227 (M+1)+.

후처리

  1. temperatureIt was cooled to ambient temperature
  2. extractionextracted with EtOAc (150 mL)
  3. washwashed with water, brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1 to 5:1 to 1:1)

출처 및 근거

ORD 기록
ord-efc5e3350aa945acb5f09b467ebb132c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206166B2

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