Tetrahydrofuran → HCID 19606112, compound

HRID 233668Notes

Reaction equation

HRID 233668 reaction equation
[C:1]1([N:7]2[CH:17]=[C:10]3[CH2:11][C:12]4[N:16]([C:9]3=[N:8]2)[CH:15]=[CH:14][CH:13]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1O[CH2:34][CH2:33]OCCOCCOCCOCCOC1.C[Si](C)(C)[N-:38][Si](C)(C)C.[K+].[N:46]1[CH:51]=[CH:50][C:49]([CH2:52]Cl)=[CH:48][CH:47]=1.O1[CH2:58][CH2:57][CH2:56][CH2:55]1>>[C:1]1([N:7]2[CH:17]=[C:10]3[C:11]([CH2:55][C:56]4[CH:34]=[CH:33][N:38]=[CH:58][CH:57]=4)([CH2:52][C:49]4[CH:50]=[CH:51][N:46]=[CH:47][CH:48]=4)[C:12]4[N:16]([C:9]3=[N:8]2)[CH:15]=[CH:14][CH:13]=4)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 2855718-Crown-6HCID 745714-(Chloromethyl)pyridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 15050415HCID 15050415, compound

Product 1

HCID 19606112HCID 19606112, compoundYield 4%

Procedure

To a solution of 2,4-dihydro-2-phenylpyrazolo[4,3-B]pyrrolizine (6.1 mmol) and 18-Crown-6 (6.1 mmol) in tetrahydrofuran at 0° C. was added potassium hexamethyldisilazide, followed by 4-picolyl chloride (14.6 mmol, free-based in toluene) and the reaction allowed to warm to room temperature overnight. Following normal extractive workup and purification, the title compound was isolated as a solid in 4% yield; mp 169°-170° C.; Anal calc'd. for C26H21N5 : C, 77.40; H, 5.25; N, 17.36. Found: C, 77.01; H, 5.12; N, 17.18. Mass spec m/e 404 (M+1).

Workup

  1. customextractive workup and purification

Sources & evidence

ORD record
ord-3d8fe63f7a3943f89928e631b8e4641c
Source dataset
uspto-grants-1997_01
Patent number
US05594001

Reaction notes

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