2-Bromo-3-butyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one → 3-Butyl-2-(3-cyclopropoxy-4-methoxyphenyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]-pyridazin-4-one

HRID 2097426Notes

Reaction equation

HRID 2097426 reaction equation
Br[C:2]1[N:19]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:5]2[CH:6]=[N:7][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:9](=[O:10])[C:4]=2[C:3]=1[CH2:28][CH2:29][CH2:30][CH3:31].BrC1N(COCC[Si](C)(C)C)C2C=NN(COCC[Si](C)(C)C)C(=O)C=2C=1C.[CH:60]1([O:63][C:64]2[CH:65]=[C:66](B3OC(C)(C)C(C)(C)O3)[CH:67]=[CH:68][C:69]=2[O:70][CH3:71])[CH2:62][CH2:61]1.C1(OC2C=C(B3OC(C)(C)C(C)(C)O3)C=CC=2OC(F)F)CC1>>[CH2:28]([C:3]1[C:4]2[C:9](=[O:10])[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:7]=[CH:6][C:5]=2[N:19]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:2]=1[C:66]1[CH:67]=[CH:68][C:69]([O:70][CH3:71])=[C:64]([O:63][CH:60]2[CH2:61][CH2:62]2)[CH:65]=1)[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 4

HCID 666024822-Bromo-3-butyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 666025852-(3-Cyclopropoxy-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 666027042-Bromo-3-methyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 666028342-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Product 1

HCID 666024283-Butyl-2-(3-cyclopropoxy-4-methoxyphenyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]-pyridazin-4-oneYield 88%

Procedure

Reaction and post treatment were carried out in the same manner as in Example 4-(a) except for using 530 mg (0.999 mmol) of 2-bromo-3-butyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in the following Reference example 22-(b) in place of 2-bromo-3-methyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one, and using 435 mg (1.50 mmol) of 2-(3-cyclopropoxy-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane obtained in the following Reference Example 1-(e) in place of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, whereby 537 mg of the title compound was obtained as a brownish oil. (Yield: 88%)

Workup

  1. customReaction and post treatment

Sources & evidence

ORD record
ord-4a0f9ef55f91429db8dde4253c9e84da
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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