Acetonitrile → {3-[3-(2-methoxy-pyridin-3-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-morpholin-4-yl-methanone

HRID 1865583ノート

反応式

HRID 1865583 の反応式
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[O:18])[CH:14]=[CH:15][CH:16]=3)[CH:9]=2)[N:4]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[N:3]=1.F[C:34](F)(F)[C:35]1C=C(B(O)O)[CH:38]=[CH:39][CH:40]=1.[C:46](=[O:49])([O-])[O-].[Na+].[Na+].C(#[N:54])C>[Br-].[Na+].C(OCC)(=O)C>[CH3:46][O:49][C:34]1[C:35]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:12]=[C:13]([C:17]([N:19]5[CH2:24][CH2:23][O:22][CH2:21][CH2:20]5)=[O:18])[CH:14]=[CH:15][CH:16]=4)[CH:9]=3)[N:4]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[N:3]=2)=[CH:40][CH:39]=[CH:38][N:54]=1

参加物

7

反応物 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 59836119(3-(3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)phenyl)(morpholino)methanone

生成物 1

HCID 68617336{3-[3-(2-methoxy-pyridin-3-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-morpholin-4-yl-methanone収率 116%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 253881Sodium Bromide溶媒

実験手順

A mixture of {3-[3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-morpholin-4-yl-methanone (33 mg, 66% pure, 38 μmol), 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichlormethane adduct (5 mg, 6 μmol) and 3-trifluoromethylphenylboronic acid (14 mg, 92 μmol) in acetonitrile (2 mL) and 2 M solution of sodium carbonate (1 mL) was irradiated in a Personal Chemistry Optimizer at 175° C. for 20 min. The crude reaction mixture was diluted with saturated aqueous solution of sodium bromide (1 mL) and ethyl acetate (4 mL) and the organic phase separated, adsorbed onto silica and purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes to afford {3-[3-(2-methoxy-pyridin-3-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-morpholin-4-yl-methanone (24 mg, 116% yield) as an off-white residue. MS: m/z 568 [MNa+], 546 [MH+], 428 [MH+-(Me3Si(CH2)2O)]

後処理

  1. customwas irradiated in a Personal Chemistry Optimizer at 175° C. for 20 min
  2. customThe crude reaction mixture
  3. customthe organic phase separated
  4. custompurified by flash silica gel chromatography

出典と根拠

ORDレコード
ord-f7e1fd5b0e194a8fac3a9675a51eb3cd
出典データセット
uspto-grants-2009_12
特許番号
US07626021B2

反応ノート

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