Methylboronic Acid → 5-Benzyloxymethyl-3-methyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097503Notes

Reaction equation

HRID 2097503 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]2[C:17](Br)=[CH:18][N:19]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:13]=2[CH:12]=[N:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:30]1C2C(=O)N(COCC[Si](C)(C)C)N=CC=2N(COCC[Si](C)(C)C)C=1.CB(O)O>>[CH2:1]([O:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]2[C:17]([CH3:30])=[CH:18][N:19]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:13]=2[CH:12]=[N:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 139377Methylboronic AcidHCID 666025033-Bromo-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 666028565-Benzyloxymethyl-3-bromo-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 666028505-Benzyloxymethyl-3-methyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 96%

Procedure

Reaction and post treatment were carried out in the same manner as in Reference example 20-(b) except for using 30.8 g (66.3 mmol) of 5-benzyloxymethyl-3-bromo-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 24-(b) in place of 3-bromo-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one, and using 12.0 g (200 mmol) of methylboronic acid in place of propylboronic acid, respectively, whereby 25.3 g of the title compound was obtained as a brownish oil. (Yield: 96%)

Workup

  1. customReaction and post treatment

Sources & evidence

ORD record
ord-b0e63192eb424a12b77b74e1c801d405
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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