Water → HCID 19892171, compound

HRID 893377Notes

Reaction equation

HRID 893377 reaction equation
[CH2:1]([C:4]1[NH:12][C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=1)[CH2:2][CH3:3].[H-].[Na+].[C:15]1([C:21]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:22]2[C:26]([C:27]3[C:32]([C:33]4[CH:38]=[CH:37][C:36]([CH2:39]Br)=[CH:35][CH:34]=4)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:25][N:24]=[N:23]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C=O)C>[CH2:1]([C:4]1[N:12]([CH2:39][C:36]2[CH:35]=[CH:34][C:33]([C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:26]3[N:22]([C:21]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)[C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:23]=[N:24][N:25]=3)=[CH:38][CH:37]=2)[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 189467102-Propyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 19892171HCID 19892171, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 2-propyl-1H-pyrrolo-[2,3-b]pyridine (29 mg, 0.18 mmol) in DMF (1 mL) was added NaH (6.7 mg of an 80% dispersion in oil, 0.271 mmol). After 20 min, N-triphenylmethyl-5-(4'-bromomethylbiphen-2-yl)tetrazole (111 mg, 0.19 mmol) was added and the mixture was stirred for 30 min. Water was added and the mixture was extracted with EtOAc. Purification by flash chromatography (SiO2, 25% EtOAc/hexanes) gave 2-propyl-1-[[2'-(1-triphenylmethyl-1H-tetrazol-5-yl)[1,1']-biphenyl-4-yl]methyl]-1H-pyrrolo[2,3-b]pyridine as a foam.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. customPurification by flash chromatography (SiO2, 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9b7e9fb3dcde425f9ad2edef73496113
Source dataset
uspto-grants-1992_06
Patent number
US05124335

Reaction notes

Loading…