Phosphorus oxychloride → (4-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)methanol

HRID 1445926

反応式

HRID 1445926 の反応式
[CH2:1]([N:8]1[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]1[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl.C(N1C=CC=C1C)C1C=CC=CC=1.C([O:36][C:37]([C:39]1[NH:49][C:42]2=[N:43][CH:44]=[CH:45][C:46]([O:47][CH3:48])=[C:41]2[CH:40]=1)=O)C>O1CCCC1.CN(C)C=O>[CH2:1]([N:8]1[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]1[CH:14]=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH3:48][O:47][C:46]1[CH:45]=[CH:44][N:43]=[C:42]2[NH:49][C:39]([CH2:37][OH:36])=[CH:40][C:41]=12

参加物

8

反応物 4

HCID 24813Phosphorus oxychlorideHCID 11736140Ethyl 4-methoxy-1H-pyrrolo[2,3-b]pyridine-2-carboxylateHCID 126430841-benzyl-2-methyl-1H-pyrroleHCID 591703801-benzyl-5-methyl-1H-pyrrole-2-carbaldehyde

生成物 2

HCID 15885418(4-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)methanolHCID 591703801-benzyl-5-methyl-1H-pyrrole-2-carbaldehyde

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

1-Benzyl-5-methyl-1H-pyrrole-2-carbaldehyde, 4: POCl3 (23.46 mL, 246 mmol) was added dropwise to a stirred N,N-dimethyformamide (204 mL) at 0° C. After addition the mixture was stirred for additional 90 minutes. To the mixture was added dropwise the solution of 1-benzyl-2-methyl-1H-pyrrole, 3 (2.71 g, 45 mmol) in tetrahydrofuran (1150 mL). The reaction mixture was allowed to be stirred for 18 h from 0° C. to room temperature. The mixture was concentrated and redissolved in ethyl acetate (2 L). The mixture was washed with saturated Na2CO3 (2×500 mL). The Na2CO3 solution was extracted with ethyl acetate (7×1 L). The organic layers were combined and concentrated. The crude product was purified by silica gel chromatography (hexane to hexane:ethyl acetate, 7:1) to afford 1-benzyl-5-methyl-1H-pyrrole-2-carbaldehyde, 4 as a light yellow liquid. Yield: 30.8 g (81%).

後処理

  1. additionAfter addition the mixture
  2. stirringto be stirred for 18 h from 0° C. to room temperature
  3. concentrationThe mixture was concentrated
  4. dissolutionredissolved in ethyl acetate (2 L)
  5. washThe mixture was washed with saturated Na2CO3 (2×500 mL)
  6. extractionThe Na2CO3 solution was extracted with ethyl acetate (7×1 L)
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography (hexane to hexane:ethyl acetate, 7:1)

出典と根拠

ORDレコード
ord-156d251a788a494ea4ce7d0095a8794d
出典データセット
uspto-grants-2010_02
特許番号
US07666898B2

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