Sodium triacetoxyborohydride → 2-(4-(1,1-Dimethylethyl)phenyl)-8-((1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)amino)-1(2H)-phthalazinone

HRID 133107

反応式

HRID 133107 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1)[N:8]=[CH:7]2.[NH:23]1[C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[C:25]([CH:32]=O)=[CH:24]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:20][C:19]([C:16]1[CH:15]=[CH:14][C:13]([N:9]2[N:8]=[CH:7][C:6]3[C:11](=[C:2]([NH:1][CH2:32][C:25]4[C:26]5[C:27](=[N:28][CH:29]=[CH:30][CH:31]=5)[NH:23][CH:24]=4)[CH:3]=[CH:4][CH:5]=3)[C:10]2=[O:12])=[CH:18][CH:17]=1)([CH3:22])[CH3:21]

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 691606278-amino-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one

生成物 1

HCID 116259932-(4-(1,1-Dimethylethyl)phenyl)-8-((1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)amino)-1(2H)-phthalazinone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 8-amino-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one (Example 1, Step E, 0.36 g, 1.1 mmol, 1 eq) and CH2Cl2 (50 mL) was added 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (0.16 g, 1.1 mmol, 1 eq) and NaBH(OAc)3 (0.72 g, 3.4 mmol, 3.0 eq). The reaction was stirred at RT for 12 h then quenched with H2O and extracted with CH2Cl2. The organic layer was washed with H2O and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by silica flash chromatography (10-75% EtOAc:hexane) to give the desired product as a yellow solid. MS m/e 424 (M+H)+. Calc'd for C26H25N5O-423.51.

後処理

  1. customthen quenched with H2O
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica flash chromatography (10-75% EtOAc:hexane)

出典と根拠

ORDレコード
ord-27cc4fb6d8be4f56838139a945ac0d5d
出典データセット
uspto-grants-2008_06
特許番号
US07390820B2

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