Water → [6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol

HRID 2279125ノート

反応式

HRID 2279125 の反応式
Br[C:2]1[N:7]=[C:6]2[N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:9]=[C:10]([CH3:11])[C:5]2=[C:4]([CH2:18][OH:19])[CH:3]=1.[CH3:20][O:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].O>COCCOC.O.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[Pd].C(OCC)(=O)C>[CH3:20][O:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[N:7]=[C:6]3[N:8]([CH:12]4[CH2:17][CH2:16][CH2:15][CH2:14][O:13]4)[N:9]=[C:10]([CH3:11])[C:5]3=[C:4]([CH2:18][OH:19])[CH:3]=2)=[CH:26][CH:25]=1

参加物

8

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27625284-(Methoxymethoxy)phenylboronic acid2 回HCID 90014303[6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol

生成物 1

HCID 90013757[6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol収率 103.2%

試薬・触媒・溶媒 3

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)触媒HCID 8857Ethyl Acetate溶媒HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

To a degassed mixture of 141 mg [6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol, 95 mg 4-(methoxymethoxy)phenylboronic acid and 65 mg potassium carbonate in DME/water (v/v=2/1, 2.3 mL) at r.t. and under Ar-atmosphere 6 mg palladium(0) bis(tri-tert-butylphosphine) was added and the mixture was stirred at 85° C. for 40 min in a microwave reactor. Then 6 mg palladium(0) bis(tri-tert-butylphosphine) and 95 mg 4-(methoxymethoxy)phenylboronic acid were added and the mixture was stirred at 100° C. for 20 min. To the mixture water and ethyl acetate were added, the phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were concentrated in vacuo and the residue was triturated with ethyl acetate. The resulting solid was isolated by filtration. 171 mg (100%) of the title compound were obtained.

後処理

  1. additionunder Ar-atmosphere 6 mg palladium(0) bis(tri-tert-butylphosphine) was added
  2. stirringthe mixture was stirred at 100° C. for 20 min
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. concentrationThe combined organic phases were concentrated in vacuo
  6. customthe residue was triturated with ethyl acetate
  7. customThe resulting solid was isolated by filtration

出典と根拠

ORDレコード
ord-37639837d83547b69c2bec0682cd4f89
出典データセット
uspto-grants-2015_09
特許番号
US09133181B2

反応ノート

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