Sodium Carbonate → 4-tert-butyl-N-(7-(3-(hydroxymethyl)phenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide

HRID 1409136ノート

反応式

HRID 1409136 の反応式
[C:1]([C:5]1[CH:24]=[CH:23][C:8]([C:9]([NH:11][C:12]2[CH:17]=[C:16](Cl)[N:15]3[N:19]=[C:20]([CH3:22])[CH:21]=[C:14]3[N:13]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH:25][CH2:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.C([O-])([O-])=O.[Na+].[Na+]>N#N.[Cl-].[Na+].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>[C:1]([C:5]1[CH:24]=[CH:23][C:8]([C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:31]3[CH:30]=[CH:29][CH:28]=[C:27]([CH2:26][OH:25])[CH:32]=3)[N:15]3[N:19]=[C:20]([CH3:22])[CH:21]=[C:14]3[N:13]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 866522574-tert-butyl-N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide2 回

生成物 1

HCID 442325004-tert-butyl-N-(7-(3-(hydroxymethyl)phenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide収率 62%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 947Nitrogen溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
100 °C

実験手順

A suspension of 4-tert-butyl-N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide (1K, 40 mg, 1.0 equivalent), 3-(hydroxymethyl)phenylboronic acid (1.9 equivalents), Pd(PPh3)4 (0.10 equivalent), and Na2CO3 (4.0 equivalents) in N2-saturated 5:1 DMF/H2O (0.05 M with respect to 1K) was stirred at 100° C. overnight. After cooling, the mixture was diluted with brine and extracted with EtOAc. Combined organic layers were dried over MgSO4, filtered and concentrated. The crude product was purified by chromatography (SiO2, gradient of 40 to 50% EtOAc/hexanes). The product was then recrystallized from CH2Cl2-hexanes to give the titled compound (62%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.37 (s, 9H) 2.50 (s, 3H) 4.83 (d, J=6.1 Hz, 2H) 6.29 (s, 1H) 7.44-7.71 (m, 5H) 7.88 (d, J=8.3 Hz, 2H) 8.03 (s, 1H) 8.15 (s, 1H) 8.59 (s, 1H).

後処理

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. dry with materialCombined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by chromatography (SiO2, gradient of 40 to 50% EtOAc/hexanes)
  7. customThe product was then recrystallized from CH2Cl2-hexanes

出典と根拠

ORDレコード
ord-dac96a52a1ff449d969e19d94cdd1688
出典データセット
uspto-grants-2014_12
特許番号
US08921358B2

反応ノート

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