Sodium Carbonate → HCID 178482403、化合物

HRID 33410

反応式

HRID 33410 の反応式
I[C:2]1[CH:10]2[CH:5]([N:6]=[CH:7][N:8]=[C:9]2[NH:11][CH3:12])[N:4]([CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=1.COC(O)C(O)OC.[OH:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[OH:30][C:31]1[CH:36]=[C:35]([C:2]2[CH:10]3[CH:5]([N:6]=[CH:7][N:8]=[C:9]3[NH:11][CH3:12])[N:4]([CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=2)[CH:34]=[CH:33][CH:32]=1

参加物

5

反応物 4

HCID 10340Sodium CarbonateHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 21263609Dimethoxy ethylene glycolHCID 178482405HCID 178482405、化合物

生成物 1

HCID 178482403HCID 178482403、化合物

実験手順

t-butyl 3-(5-iodo-4-(methylamino)-4aH-pyrrolo[2,3-d]pyrimidin-7(7aH)-yl)propanoate (123 mmol) from above was placed in a 25 ml round bottom flask, whereupon 3.1 ml dimethoxy ethyleneglycol was added. 3-Hydroxyphenylboronic acid (492 mmol pre-dissolved in 0.66 ml ethanol) was added at once, and was followed by 0.5 ml saturated aqueous sodium carbonate. Pd0(PPh3)4 (14 mg, 12 umol) was added to the reaction, the vessel was purged with argon, and set to stir at 80 C overnight. The reaction was subsequently cooled, and filtered through a bed of celite. The filtrate was evaporated in vacuo, and the residual material was adhered to silica gel using ethyl acetate as solvent. Silica gel chromatography (ethyl acetate:hexanes) and evaporation in vacuo of the requisite fractions yielded the desired product. MS m/z=369.22.

後処理

  1. additionwas added
  2. customthe vessel was purged with argon
  3. temperatureThe reaction was subsequently cooled
  4. filtrationfiltered through a bed of celite
  5. customThe filtrate was evaporated in vacuo
  6. customSilica gel chromatography (ethyl acetate:hexanes) and evaporation in vacuo of the requisite fractions

出典と根拠

ORDレコード
ord-94c38d12c62f4e1893c38f6dd209baac
出典データセット
uspto-grants-2008_09
特許番号
US07429596B2

関連ノート

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