Diethyl Ether → HCID 57893455、化合物

HRID 1821849

反応式

HRID 1821849 の反応式
[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

参加物

6

反応物 4

HCID 3283Diethyl Ether2 回HCID 25517Ammonium ChlorideHCID 578935037-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehydeHCID 178418255HCID 178418255、化合物2 回

生成物 1

HCID 57893455HCID 57893455、化合物収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-15 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e8ef13baa8f14ab4b618b086164db16e
出典データセット
uspto-grants-2009_10
特許番号
US07608627B2

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