Nitrogen → 5-[7-(4-Fluoro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-pyridin-3-ylamine

HRID 341193노트

반응식

HRID 341193 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[CH:14]=[CH:15][N:16]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:19]=[N:20][CH:21]=[C:22](Br)[CH:23]=1.C([O-])([O-])=O.[K+].[K+].N#N>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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14]([C:22]4[CH:23]=[C:18]([NH2:17])[CH:19]=[N:20][CH:21]=4)=[CH:15][N:16]=[C:10]3[CH:9]=2)=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 8176813-Amino-5-bromopyridine2회HCID 593207997-(4-Fluoro-phenyl)-imidazo[1,2-a]pyridine

생성물 1

HCID 593211075-[7-(4-Fluoro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-pyridin-3-ylamine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매2회HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

To 7-(4-fluoro-phenyl)-imidazo[1,2-a]pyridine (0.1093 g, 0.52 mmol) and 3-amino-5-bromopyridine (0.181 g, 1.05 mmol) in DMF (2 mL) was added 0.5 M K2CO3 (2.06 mL, 1.03 mmol). The reaction vessel was purged with N2 and Pd(PPh3)4 (63 mg, 0.055 mmol) added. The vessel was further purged with N2 and then heated in the microwave at 120° C. for 30 mins. Further 3-amino-5-bromopyridine (0.13 g, 0.75 mmol) and Pd(PPh3)4 (43 mg, 0.037 mmol) were added and the reaction heated in the microwave at 140° C. for 1 hour. The solids were filtered and the filtrate was concentrated in vacuo. The residue was partitioned between H2O (20 ml) and EtOAc (2×20 mL). The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo and the product used crude in the subsequent reaction.

후처리

  1. additionadded
  2. customThe vessel was further purged with N2
  3. temperaturethe reaction heated in the microwave at 140° C. for 1 hour
  4. filtrationThe solids were filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was partitioned between H2O (20 ml) and EtOAc (2×20 mL)
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customin the subsequent reaction

출처 및 근거

ORD 기록
ord-d0fec6e4f8084c1d8ebd539e025d9d5e
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895745B2

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