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

HRID 2279125노트

반응식

HRID 2279125 반응식
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

참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27625284-(Methoxymethoxy)phenylboronic acid2회HCID 90014303[6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol

생성물 1

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

시약·촉매·용매 3

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)촉매HCID 8857Ethyl Acetate용매HCID 18180031Water 1,2-dimethoxyethane용매

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온도
85 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-37639837d83547b69c2bec0682cd4f89
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133181B2

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