Phenylboronic Acid → 1,5-Bis(2-trimethylsilylethoxymethyl)-3-[1-(2-trimethylsilylethoxymethyl)-4-pyrazolyl]-1,5-dihydropyrrolo-[2,3-d]pyridazin-4-one

HRID 2097514Notes

Reaction equation

HRID 2097514 reaction equation
Br[C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[N:7]=[CH:6][C:5]=2[N:4]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:3]=1.ClC1[N:38]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:32]2C=N[NH:35][C:36](=O)[C:31]=2C=1I.CC1(C)C(C)(C)OB(C2C=NN(COCC[Si](C)(C)C)C=2)O1.C1(B(O)O)C=CC=CC=1>>[CH3:25][Si:24]([CH3:27])([CH3:26])[CH2:23][CH2:22][O:21][CH2:20][N:4]1[C:5]2[CH:6]=[N:7][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:9](=[O:11])[C:10]=2[C:2]([C:31]2[CH:36]=[N:35][N:38]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:32]=2)=[CH:3]1

Participants

5

Reactant 4

HCID 66827Phenylboronic AcidHCID 574776664-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazoleHCID 666025033-Bromo-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 666028262-Chloro-3-iodo-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 666026681,5-Bis(2-trimethylsilylethoxymethyl)-3-[1-(2-trimethylsilylethoxymethyl)-4-pyrazolyl]-1,5-dihydropyrrolo-[2,3-d]pyridazin-4-oneYield 46%

Procedure

Reaction and post treatment were carried out in the same manner as in Reference example 31 except for using 289 mg (0.61 mmol) of 3-bromo-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 20-(a) in place of 2-chloro-3-iodo-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]-pyridazin-4-one, and using 619 mg (1.91 mmol) of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilylethoxymethyl)-1H-pyrazole obtained in Reference example 32-(a) in place of phenylboronic acid, respectively, whereby 166 mg of the title compound was obtained as a slightly yellowish oil. (Yield: 46%)

Workup

  1. customReaction and post treatment

Sources & evidence

ORD record
ord-ae54dc7439dc4b03a3d4c15987e56073
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

Loading…