Toluene → HCID 57477669, compound

HRID 1426559Notes

Reaction equation

[NH:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:10]=[CH:11][C:4]=12)[NH2:2].[O:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[CH:29]([CH:32]=O)[CH:30]=O.C1(C)C=CC=CC=1>>[CH3:17][Si:16]([CH3:19])([CH3:18])[CH2:15][CH2:14][O:13][CH2:12][N:9]1[C:5]2=[N:6][CH:7]=[CH:8][C:3]([N:1]3[CH:30]=[C:29]([C:21]4[O:20][C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[N:22]=4)[CH:32]=[N:2]3)=[C:4]2[CH:11]=[CH:10]1

Participants

Reactant 3

HCID 1140Toluene

HCID 38276322-(2-Benzoxazolyl)malondialdehyde

HCID 57477670HCID 57477670, compound

Product 1

HCID 57477669HCID 57477669, compoundYield 69.5%

Conditions

Temperature: 70 °C

Procedure

To 4-hydrazino-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine (0.083 g, 0.00030 mol) 3782-117-1 and 1,3-benzoxazol-2-ylmalonaldehyde (0.056 g, 0.00030 mol) in toluene (1.5 mL, 0.014 mol) was added molecular sieves. The mixture was heated in a sealed tube at 70° C. (an oil bath) with stilling for 2 h. The solvent was removed in vacuo and the crude product was purified by FCC on silica using ethyl acetate:hexanes 3:7 to give 2-[1-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-4-yl]-1,3-benzoxazole (0.090 gm) as an oil, LC/MS (M+H)+: 432.

Workup

customThe solvent was removed in vacuo
customthe crude product was purified by FCC on silica

Sources & evidence

ORD record: ord-a069cf0a1a3c483687f056c938c2f317
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933086B2

Reaction notes

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