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1H-Indole-4-boronic acid → HCID 68195323、化合物

HRID 1631764
ノート
印刷プレビュー

反応式

HRID 1631764 の反応式
[C:1]([O:4][C:5]([CH3:25])([CH2:7][CH2:8][CH2:9][N:10]1[CH2:19][C@@H:18]2[CH2:20][O:21][CH2:22][CH2:23][N:17]2[C:16]2[N:15]=[C:14](Cl)[N:13]=[CH:12][C:11]1=2)[CH3:6])(=[O:3])[CH3:2].[NH:26]1[C:34]2[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[C:29]=2[CH:28]=[CH:27]1>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:1]([O:4][C:5]([CH3:25])([CH2:7][CH2:8][CH2:9][N:10]1[CH2:19][C@@H:18]2[CH2:20][O:21][CH2:22][CH2:23][N:17]2[C:16]2[N:15]=[C:14]([C:30]3[CH:31]=[CH:32][CH:33]=[C:34]4[C:29]=3[CH:28]=[CH:27][NH:26]4)[N:13]=[CH:12][C:11]1=2)[CH3:6])(=[O:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 27631731H-Indole-4-boronic acidHCID 86670148HCID 86670148、化合物

生成物 1

HCID 68195323HCID 68195323、化合物収率 27%

試薬・触媒・溶媒 1

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒

反応条件

温度
120 °C

実験手順

To a 2 mL microwave vial were added (R)-5-(2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)-2-methylpentan-2-yl acetate (PREPARATION x81, 148 mg, 0.401 mmol), indole-4-boronic acid (64.6 mg, 0.401 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (16.50 mg, 0.020 mmol). The vial was evacuated and filled with nitrogen. After sealing the vial, dioxane (1600 μL) and saturated NaHCO3 (400 μL) were added. The mixture was then heated in a microwave to 120° C. for 45 minutes. After the mixture was cooled to room temperature, ACN (4 mL) was added and the mixture was filtered by syringe filter. The crude product was purified by preparatory HPLC using a gradient of 20-40% CH3CN (with 0.035% TFA) in H2O (with 0.05% TFA). The collected fractions were pooled, neutralized with NaHCO3, concentrated, and extracted with EtOAc. The combined organics were dried over MgSO4, filtered, and concentrated to give the title compound (48 mg, 27%). ESI-MS m/z [M+H]+ calc'd for C25H31N5O3, 450.25. found 450.3.

後処理

  1. customThe vial was evacuated
  2. additionfilled with nitrogen
  3. additionwere added
  4. temperatureAfter the mixture was cooled to room temperature
  5. additionACN (4 mL) was added
  6. filtrationthe mixture was filtered by syringe
  7. filtrationfilter
  8. customThe crude product was purified by preparatory HPLC
  9. concentrationconcentrated
  10. extractionextracted with EtOAc
  11. dry with materialThe combined organics were dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated

出典と根拠

ORDレコード
ord-ee5302eb83724479925297b9f0edc3f8
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08791107B2

反応ノート

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