Triphenylphosphine → 3-(1-(4-((R)-tetrahydrofuran-3-yloxy)-2,3-difluorophenyl)-1H-tetrazol-5-yl)-5-bromopyridin-2-amine

HRID 446740

반응식

HRID 446740 반응식
[NH2:1][C:2]1[C:7]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([F:20])[C:14]=3[F:21])[N:11]=[N:10][N:9]=2)=[CH:6][C:5]([Br:22])=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:42]1[CH2:46][CH2:45][C@H:44](O)[CH2:43]1>C1COCC1>[O:42]1[CH2:46][CH2:45][C@@H:44]([O:19][C:16]2[CH:17]=[CH:18][C:13]([N:12]3[C:8]([C:7]4[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([Br:22])[CH:6]=4)=[N:9][N:10]=[N:11]3)=[C:14]([F:21])[C:15]=2[F:20])[CH2:43]1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 2733227(S)-(+)-3-HydroxytetrahydrofuranHCID 582937904-(5-(2-amino-5-bromopyridin-3-yl)-1H-tetrazol-1-yl)-2,3-difluorophenol

생성물 1

HCID 582937713-(1-(4-((R)-tetrahydrofuran-3-yloxy)-2,3-difluorophenyl)-1H-tetrazol-5-yl)-5-bromopyridin-2-amine수율 92.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of Compound 1086 (90 mg, 0.2438 mmol), triphenylphosphine (76.74 mg, 0.2926 mmol), diisoproplylazodicarboxylate (59.17 mg, 56.68 μL, 0.2926 mmol), and (S)-tetrahydrofuran-3-ol (25.78 mg, 0.2926 mmol) in THF (90 μL) was heated at 70° C. for 10 minutes under microwave irradiation. The reaction was quenched with ammonium chloride (satd') and extracted with EtOAc. The organics were washed with 1 M NaOH (2×), brine, dried over sodium sulfate, and concentrated under vacuum. The residue was chromatographed over silica gel (0-50% EtOAc/hexanes gradient) to give 3-(1-(4-((R)-tetrahydrofuran-3-yloxy)-2,3-difluorophenyl)-1H-tetrazol-5-yl)-5-bromopyridin-2-amine (Compound 1090, 99 mg).

후처리

  1. customThe reaction was quenched with ammonium chloride (satd') and
  2. extractionextracted with EtOAc
  3. washThe organics were washed with 1 M NaOH (2×), brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was chromatographed over silica gel (0-50% EtOAc/hexanes gradient)

출처 및 근거

ORD 기록
ord-5ea3c27186d64bf1b1e51b79fc6b0e78
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481524B2

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