Sodium Carbonate → 6-(3-Hydroxyphenyl)-2-(4-phenoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 64376

反応式

HRID 64376 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:14]=3)[C:10]=2[C:11]#[N:12])[CH:7]=1.[OH:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:26][C:27]1[CH:32]=[C:31]([C:2]2[CH:3]=[N:4][C:5]3[N:6]([N:8]=[C:9]([C:13]4[CH:18]=[CH:17][C:16]([O:19][C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:15][CH:14]=4)[C:10]=3[C:11]#[N:12])[CH:7]=2)[CH:30]=[CH:29][CH:28]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 1176680926-Bromo-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

生成物 1

HCID 1176681096-(3-Hydroxyphenyl)-2-(4-phenoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrile収率 62%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
65 °C

実験手順

To a solution of 6-bromo-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (782 mg, 2.0 mmol) in dioxane (10 mL) and H2O (10 mL) was added 3-hydroxyphenylboronic acid (276 mg, 2.0 mmol), Pd(PPh3)4 (240 mg, 0.2 mmol) and Na2CO3 (424 mg, 4.0 mmol). After stirring at 65° C. under N2 for 16 hr, the mixture was concentrated and 100 mL of DCM, 10 mL of CH3OH, 100 mL of H2O were added. Organic layers were separated from aqueous layers and dried over Na2SO4 and purified by chromatography column on silica gel eluting with DCM/CH3OH to afford 500 mg (62%) of 6-(3-hydroxyphenyl)-2-(4-phenoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrile as a yellow solid. MS (ESI) m/e [M+1]+ 404.9.

後処理

  1. concentrationthe mixture was concentrated
  2. addition100 mL of DCM, 10 mL of CH3OH, 100 mL of H2O were added
  3. customOrganic layers were separated from aqueous layers
  4. dry with materialdried over Na2SO4
  5. custompurified by chromatography column on silica gel eluting with DCM/CH3OH

出典と根拠

ORDレコード
ord-ef099b0ab4d746cc97e8ec35a5a8e201
出典データセット
uspto-grants-2016_09
特許番号
US09447106B2

関連ノート

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