Diethyl Ether → HCID 57893455, 화합물

HRID 1821849

반응식

HRID 1821849 반응식
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([CH:18]=[O:19])[NH:15][C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]1([Mg]Br)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCOCC.[Cl-].[NH4+]>O1CCCC1>[CH2:20]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([CH:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[OH:19])[NH:15][C:14]=12)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 3283Diethyl Ether2회HCID 25517Ammonium ChlorideHCID 578935037-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehydeHCID 178418255HCID 178418255, 화합물2회

생성물 1

HCID 57893455HCID 57893455, 화합물수율 62%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-15 °C

실험 절차

To a solution of 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (Example 141) (1.7 g, 5.1 mmol) in tetrahydrofuran (25 mL) was added 3.0 M phenylmagnesium bromide in Et2O (2.0 mL, 6 mmol) dropwise at −78° C. under a nitrogen atmosphere. After stirring for ca. 2 h, additional 3.0 M phenylmagnesium bromide in Et2O (2.0 mL, 6 mmol) was added. The reaction mixture was stirred for another 1.5 h warming to −15° C. The reaction mixture was poured into a saturated ammonium chloride solution, and extracted with ethyl acetate (3×). The combined organic extracts were washed with saturated sodium chloride, and dried over sodium sulfate. Filtration and concentration provided the crude material, which was purified by Biotage chromatography (10-30% ethyl acetate in hexanes) to provide [7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanol (1.32 g, 62%) as a yellow foam: mp 53-61° C.; 1H NMR (500 MHz, CD3OD) δ4.60 (4H, q, J=23.2, 15.4 Hz), 5.95 (1H, s), 6.25 (1H, s), 7.05 (1H, d, J=5.7 Hz), 7.15-7.40 (15H, m), 7.62 (1H, d, J=5.7 Hz); ESI MS m/z 420 [C28H25N3O+H]+; HPLC (Method A) >99% (AUC), tR=19.2 min.

후처리

  1. stirringThe reaction mixture was stirred for another 1.5 h
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic extracts were washed with saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration
  6. customprovided the crude material, which
  7. customwas purified by Biotage chromatography (10-30% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-e8ef13baa8f14ab4b618b086164db16e
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608627B2

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