Hydrochloric Acid → 9-Benzenesulfonyl-5-hydroxy-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 60216ノート

反応式

HRID 60216 の反応式
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=3[C:12]3[CH:22]=[C:23](Br)[CH:24]=[N:25][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.C(OCC)(=O)C.Cl>[Pd].C(N(CC)CC)C.CN(C=O)C>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=3[C:12]3[CH:22]=[CH:23][CH:24]=[N:25][C:11]2=3)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8857Ethyl AcetateHCID 582664728-(Benzenesulfonyl)-12-bromo-3-hydroxy-5,8,10-triazatricyclo[7.4.0.02,7]trideca-1(9),2,4,6,10,12-hexaene-4-carbonitrile

生成物 1

HCID 582663029-Benzenesulfonyl-5-hydroxy-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile収率 89%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

A mixture of 9-benzenesulfonyl-3-bromo-5-hydroxy-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (9.91 g, 23.1 mmol), palladium on carbon hydrogenation catalyst (10 wt %, 1.0 g, 0.94 mmol), ethanol (250 mL), ethyl acetate (50 mL), DMF (50 mL) and triethylamine (50 mL) was stirred at room temperature under an atmosphere of hydrogen for 16 hours. The catalyst was removed by filtration through Celite© and the filtrate evaporated to dryness to give a gum, that was mixed with hydrochloric acid (1M, 100 mL) and sonicated in a laboratory ultrasonic cleaning bath for 30 minutes. The resultant solid was collected by filtration, washed with water then dried under vacuum to afford the title compound as a tan coloured solid (7.19 g, 89%). 1H NMR (400 MHz, DMSO-d6): 9.27 (s, 1H), 8.71 (dd, J=4.9, 1.7 Hz, 1H), 8.68 (dd, J=7.9, 1.7 Hz, 1H), 8.20-8.20 (m, 2H), 7.74-7.73 (m, 1H), 7.60-7.59 (m, 3H).

後処理

  1. customThe catalyst was removed by filtration through Celite©
  2. customthe filtrate evaporated to dryness
  3. customto give a gum, that
  4. customsonicated in a laboratory
  5. customfor 30 minutes
  6. filtrationThe resultant solid was collected by filtration
  7. washwashed with water
  8. customthen dried under vacuum

出典と根拠

ORDレコード
ord-64fcaa30da704c2cabb77b0d31134ccd
出典データセット
uspto-grants-2016_09
特許番号
US09440976B2

反応ノート

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