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Sodium hydride → 1-[3-{2(E)-(7-Chloroquinolin-2-yl)ethenyl}benzyl]-7-trityloxy-indole

HRID 1198537
Notes
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Reaction equation

HRID 1198537 reaction equation
[H-].[Na+].[C:3]([O:22][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:31]=1[NH:30][CH:29]=[CH:28]2)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:32][C:33]1[CH:42]=[C:41]2[C:36]([CH:37]=[CH:38][C:39](/[CH:43]=[CH:44]/[C:45]3[CH:46]=[C:47]([CH:50]=[CH:51][CH:52]=3)[CH2:48]Cl)=[N:40]2)=[CH:35][CH:34]=1.[Cl-].[NH4+]>CN(C)C=O>[Cl:32][C:33]1[CH:42]=[C:41]2[C:36]([CH:37]=[CH:38][C:39](/[CH:43]=[CH:44]/[C:45]3[CH:46]=[C:47]([CH:50]=[CH:51][CH:52]=3)[CH2:48][N:30]3[C:31]4[C:27](=[CH:26][CH:25]=[CH:24][C:23]=4[O:22][C:3]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=4)[CH:28]=[CH:29]3)=[N:40]2)=[CH:35][CH:34]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 150540107-(Triphenylmethoxy)-1H-indoleHCID 19369489trans-3-[2-(7-Chloroquinolin-2-yl)ethenyl]benzyl chloride

Product 1

HCID 191026091-[3-{2(E)-(7-Chloroquinolin-2-yl)ethenyl}benzyl]-7-trityloxy-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

60% Sodium hydride dispersion in mineral oil (44 mg 1.1 mmol) was added to a stirred solution of 7-trityloxyindole (Example 12a) (375 mg, 1.0 mmol) in dimethylformamide (4 ml). The mixture was stirred for 10 minutes at room temperature then a suspension of 3-[2(E)-(7-chloroquinolin-2-yl)ethenyl]benzyl chloride (Example 6a) (251 mg, 0.80 mmol) in dimethylformamide (4 ml) was added and the mixture was stirred for a further 3 hours. The dark solution was poured onto saturated ammonium chloride solution and extracted with dichloromethane. The extract was dried and evaporated under high vacuum and the residue was chromatographed on silica in ethyl acetate-hexane (1:5).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for a further 3 hours
  3. extractionextracted with dichloromethane
  4. customThe extract was dried
  5. customevaporated under high vacuum
  6. customthe residue was chromatographed on silica in ethyl acetate-hexane (1:5)

Sources & evidence

ORD record
ord-527e08840fc54af29c1c52875be36008
Source dataset
uspto-grants-1994_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05281593

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes